2.02012-05-31 10:21:54 -06002015-09-13 12:56:06 -0600ECMDB00148M2MDB000055L-GlutamateGlutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. Glutamate is a key molecule in cellular metabolism. There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid is found naturally primarily in the cell walls of certain bacteria. The carboxylate anions and salts of glutamic acid are known as glutamates. Glutamate is a key compound in cellular metabolism. Glutamic acid is often used as a food additive and flavour enhancer in the form of its sodium salt monosodium glutamate (MSG). Transamination of ¦Á-ketoglutarate gives glutamate. Glutamate will also go through transamination reactions with other ¦Á-ketoacids. α-aminoglutarateα-aminoglutaric acid(2S)-2-Aminopentanedioate(2S)-2-Aminopentanedioic acid(S)-(+)-Glutamate(S)-(+)-Glutamic acid(S)-2-Aminopentanedioate(S)-2-Aminopentanedioic acid(S)-Glutamate(S)-Glutamic acid1-Amino-propane-1,3-dicarboxylate1-Amino-propane-1,3-dicarboxylic acid1-Aminopropane-1,3-dicarboxylate1-Aminopropane-1,3-dicarboxylic acid2-Aminoglutarate2-Aminoglutaric acid2-Aminopentanedioate2-Aminopentanedioic acidA-AminoglutarateA-Aminoglutaric acidA-GlutamateA-Glutamic acidAciglutAlpha-AminoglutarateAlpha-Aminoglutaric acidAlpha-GlutamateAlpha-Glutamic acidAminoglutarateAminoglutaric acidEGltGluGlusateGlusic acidGlutGlutacidGlutamateGlutamic acidGlutamicolGlutamidexGlutaminateGlutaminic acidGlutaminolGlutatonL-(+)-GlutamateL-(+)-Glutamic acidL-a-AminoglutarateL-a-Aminoglutaric acidL-alpha-AminoglutarateL-alpha-Aminoglutaric acidL-GluL-GlutamateL-Glutamic acidL-GlutaminateL-Glutaminic acidL-α-AminoglutarateL-α-Aminoglutaric acidα-Aminoglutarateα-Aminoglutaric acidα-Glutamateα-Glutamic acidC5H9NO4147.1293147.053157781(2S)-2-aminopentanedioic acidL-glutamic acid56-86-0N[C@@H](CCC(O)=O)C(O)=OInChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1WHUUTDBJXJRKMK-VKHMYHEASA-NSolidCytosolExtra-organismPeriplasmlogp-3.54ALOGPSlogs-0.26ALOGPSsolubility8.06e+01 g/lALOGPSlogp-3.2ChemAxonpka_strongest_acidic1.88ChemAxonpka_strongest_basic9.54ChemAxoniupac(2S)-2-aminopentanedioic acidChemAxonaverage_mass147.1293ChemAxonmono_mass147.053157781ChemAxonsmilesN[C@@H](CCC(O)=O)C(O)=OChemAxonformulaC5H9NO4ChemAxoninchiInChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1ChemAxoninchikeyWHUUTDBJXJRKMK-VKHMYHEASA-NChemAxonpolar_surface_area100.62ChemAxonrefractivity31.29ChemAxonpolarizability13.32ChemAxonrotatable_bond_count4ChemAxonacceptor_count5ChemAxondonor_count3ChemAxonphysiological_charge-1ChemAxonformal_charge0ChemAxonGlutathione metabolismThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW000833ec00480MetabolicButanoate metabolismec00650Alanine, aspartate and glutamate metabolismec00250Arginine and proline metabolismec00330Nitrogen metabolism
The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia.
The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere.
Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK
Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia.
Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia
Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia.
Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid.
Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia.
PW000755ec00910MetabolicPurine metabolismec00230Pyrimidine metabolismThe metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.PW000942ec00240MetabolicCysteine and methionine metabolismec00270Tyrosine metabolismec00350Phenylalanine metabolismThe pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine.
Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter.
L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid.
L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP.
The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter.PW000921ec00360MetabolicPhenylalanine, tyrosine and tryptophan biosynthesisec00400Novobiocin biosynthesisec00401Carbon fixation in photosynthetic organismsec00710Isoquinoline alkaloid biosynthesisec00950Tropane, piperidine and pyridine alkaloid biosynthesisec00960Glycine, serine and threonine metabolismec00260Amino sugar and nucleotide sugar metabolismec00520Lysine biosynthesisLysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter ,
glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter
L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis).
L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine.
L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3.
A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid.PW000771ec00300MetabolicFolate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicMethane metabolismec00680Valine, leucine and isoleucine biosynthesisec00290C5-Branched dibasic acid metabolismec00660Pantothenate and CoA biosynthesisThe CoA biosynthesis requires compounds from two other pathways: aspartate metabolism and valine biosynthesis. It requires a Beta-Alanine and R-pantoate.
The compound (R)-pantoate is generated in two reactions, as shown by the interaction of alpha-ketoisovaleric acid, 5,10 methylene-THF and water through a 3-methyl-2-oxobutanoate hydroxymethyltransferase resulting in a tetrahydrofolic acid and a 2-dehydropantoate. This compound interacts with hydrogen through a NADPH driven acetohydroxy acid isomeroreductase resulting in the release of NADP and R-pantoate.
On the other hand L-aspartic acid interacts with a hydrogen ion and gets decarboxylated through an Aspartate 1- decarboxylase resulting in a carbon dioxide and a Beta-alanine.
Beta-alanine and R-pantoate interact with an ATP driven pantothenate synthetase resulting in pyrophosphate, AMP, hydrogen ion and pantothenic acid.
Pantothenic acid is phosphorylated through a ATP-driven pantothenate kinase resulting in a ADP, a hydrogen ion and D-4'-Phosphopantothenate. This compound interacts with a CTP and a L-cysteine resulting in a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a hydrogen ion, a pyrophosphate, a CMP and 4-phosphopantothenoylcysteine.
The latter compound interacts with a hydrogen ion through a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a carbon dioxide release and a 4-phosphopantetheine. This compound interacts with an ATP, hydrogen ion and an phosphopantetheine adenylyltransferase resulting in a release of pyrophosphate, and dephospho-CoA.
Dephospho-CoA reacts with an ATP driven dephospho-CoA kinase resulting in a ADP , a hydrogen ion and a Coenzyme A.
. The latter is converted into (R)-4'-phosphopantothenate is two steps, involving a β-alanine ligase and a kinase. In most organsims the ligase acts before the kinase (EC 6.3.2.1, pantoate—β-alanine ligase (AMP-forming) followed by EC 2.7.1.33, pantothenate kinase, as described in phosphopantothenate biosynthesis I and phosphopantothenate biosynthesis II. However, in archaea the order is reversed, and EC 2.7.1.169, pantoate kinase acts before EC 6.3.2.36, 4-phosphopantoate—β-alanine ligase, as described in phosphopantothenate biosynthesis III.
The kinases are feedback inhibited by CoA itself, accounting for the primary regulatory mechanism of CoA biosynthesis. The addition of L-cysteine to (R)-4'-phosphopantothenate, resulting in the formation of R-4'-phosphopantothenoyl-L-cysteine (PPC), is followed by decarboxylation of PPC to 4'-phosphopantetheine. The ultimate reaction is catalyzed by EC 2.7.1.24, dephospho-CoA kinase, which converts 4'-phosphopantetheine to CoA. All enzymes of this pathway are essential for growth.
The reactions in the biosynthetic route towards CoA are identical in most organisms, although there are differences in the functionality of the involved enzymes. In plants every step is catalyzed by single monofunctional enzymes, whereas in bacteria and mammals bifunctional enzymes are often employed [Rubio06].PW000828ec00770MetabolicVitamin B6 metabolismec00750Tryptophan metabolismThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA
PW000815ec00380MetabolicAminoacyl-tRNA biosynthesisec00970Drug metabolism - other enzymesec00983Porphyrin and chlorophyll metabolismec00860Lipopolysaccharide biosynthesisE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831ec00540MetabolicGlyoxylate and dicarboxylate metabolismec00630Histidine metabolismec00340beta-Alanine metabolismThe Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate.
Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets.PW000896ec00410MetabolicPropanoate metabolism
Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA.
Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate.
Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a
bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid.
Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA.
ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate.
Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid.
Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA.PW000940ec00640MetabolicTaurine and hypotaurine metabolismec00430D-Glutamine and D-glutamate metabolismL-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine.
L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter.
L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase.
D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis
UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase.
PW000769ec00471MetabolicValine, leucine and isoleucine degradationec00280Microbial metabolism in diverse environmentsec01120ABC transportersec02010Glucosinolate biosynthesisec00966Metabolic pathwayseco01100Amino sugar and nucleotide sugar metabolism IThe synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate.
N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively.
Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate.
N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate.
UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens.
UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism.
PW000886MetabolicAmino sugar and nucleotide sugar metabolism IIIThe synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate.
N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase.
Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose
The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate.
Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively.PW000895MetabolicAsparagine biosynthesisL-asparagine is synthesized in E. coli from L-aspartate by either of two reactions, utilizing either L-glutamine or ammonia as the amino group donor. Both reactions are ATP driven and yield AMP and pyrophosphate.
The first reaction is catalyzed only by asparagine synthetase B, while the second reaction is catalyzed by both asparagine synthetase A and asparagine synthetase B,
The only known role of asparagine in the metabolism of E. coli is as a constituent of protein. PW000813MetabolicAspartate metabolismAspartate (seen in the center) is synthesized from and degraded to oxaloacetate , an intermediate of the TCA cycle, by a reversible transamination reaction with glutamate. As shown here, AspC is the principal transaminase that catalyzes this reaction, but TyrB also catalyzes it. Null mutations in aspC do not confer aspartate auxotrophy; null mutations in both aspC and tyrB do.
Aspartate is a constituent of proteins and participates in several other biosyntheses as shown here( NAD biosynthesis and Beta-Alanine Metabolism . Approximately 27 percent of the cell's nitrogen flows through aspartate
Aspartate can be synthesized from fumaric acid through a aspartate ammonia lyase. Aspartate also participates in the synthesis of L-asparagine through two different methods, either through aspartate ammonia ligase or asparagine synthetase B.
Aspartate is also a precursor of fumaric acid. Again it has two possible ways of synthesizing it. First set of reactions follows an adenylo succinate synthetase that yields adenylsuccinic acid and then adenylosuccinate lyase in turns leads to fumaric acid. The second way is through argininosuccinate synthase that yields argininosuccinic acid and then argininosuccinate lyase in turns leads to fumaric acid
PW000787MetabolicCollection of Reactions without pathwaysPW001891MetabolicL-alanine metabolismL-alanine is an essential component of proteins and peptidoglycan. The latter also contains about three molecules of D-alanine for every L-alanine. Only about 10 percent of the total alanine synthesized flows into peptidoglycan.
There are at least 3 ways to begin the biosynthesis of alanine.
The first method for alanine biosynthesis begins with L-cysteine produced from L-cysteine biosynthesis pathway. L-cysteine reacts with an [L-cysteine desulfurase] L-cysteine persulfide through a cysteine desulfurase resulting in a release of [L-cysteine desulfurase] l-cysteine persulfide and L-alanine.
The second method starts with pyruvic acid reacting with L-glutamic acid through a glutamate-pyruvate aminotransferase resulting in a oxoglutaric acid and L-alanine.
The third method starts with L-glutamic acid interacting with Alpha-ketoisovaleric acid through a valine transaminase resulting in an oxoglutaric acid and L-valine. L-valine reacts with pyruvic acid through a valine-pyruvate aminotransferase resulting Alpha-ketoisovaleric acid and L-alanine.
This first step of the pathway, which can be catalyzed by either of two racemases( biosynthetic or catabolic), also serves an essential role in biosynthesis because its product, D-alanine, is an essential component of cell wall peptidoglycan (murein). D-alanine is metabolized by an ATP driven D-alanine ligase A and B resulting in D-alanyl-D-alanine. This product is incorporated into the peptidoglycan biosynthesis.
L-alanine is metabolized with alanine racemase, either catabolic or metabolic resulting in a D-alanine. This compound reacts with water and a quinone through a
D-amino acid dehydrogenase resulting in Pyruvic acid, hydroquinone and ammonium, thus entering the central metabolism and thereby can serve as a total source of carbon and energy. This pathway is unique among those through which L-amino acids are degraded, in that the L form must first be converted to the D form.
D-alanine, is an essential component of cell wall peptidoglycan (murein). The role of the alr racemase is predominately biosynthetic: it is produced constitutively in small amounts. The role of the dadX racemase is degradative: it is induced to high levels by alanine and is subject to catabolite repression.
PW000788MetabolicL-glutamate metabolism
There are various ways by which glutamate enters the cytoplasm in E.coli. through a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter.
There are various ways by which E. coli synthesizes glutamate from L-glutamine or oxoglutaric acid.
L-glutamine, introduced into the cytoplasm by glutamine ABC transporter, can either interact with glutaminase resulting in ammonia and L-glutamic acid, or react with oxoglutaric acid, and hydrogen ion through an NADPH driven glutamate synthase resulting in L-glutamic acid.
L-glutamic acid is metabolized into L-glutamine by reacting with ammonium through a ATP driven glutamine synthase. L-glutamic acid can also be metabolized into L-aspartic acid by reacting with oxalacetic acid through an aspartate transaminase resulting in n oxoglutaric acid and L-aspartic acid. L-aspartic acid is metabolized into fumaric acid through an
aspartate ammonia-lyase. Fumaric acid can be introduced into the cytoplasm through 3 methods:
dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, and C4 dicarboxylate / orotate:H+ symporter
PW000789MetabolicL-glutamate metabolism IIPW001886MetabolicLeucine BiosynthesisLeucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate interacting with acetyl-CoA and water through a 2-isopropylmalate synthase resulting in Coenzyme A, hydrogen Ion and 2-isopropylmalic acid. The latter compound reacts with isopropylmalate isomerase which dehydrates the compound resulting in a Isopropylmaleate. This compound reacts with water through a isopropylmalate isomerase resulting in 3-isopropylmalate. This compound interacts with a NAD-driven D-malate / 3-isopropylmalate dehydrogenase results in 2-isopropyl-3-oxosuccinate. This compound interacts spontaneously with hydrogen resulting in the release of carbon dioxide and ketoleucine. Ketoleucine interacts in a reversible reaction with L-glutamic acid through a branched-chain amino-acid aminotransferase resulting in Oxoglutaric acid and L-leucine
L-leucine can then be exported outside the cytoplasm through a transporter: L-amino acid efflux transporter.
The final step in this pathway is catalyzed by two transaminases of broad specificity, IlvE and TyrB.
Both the first enzyme in the pathway, 2-isopropylmalate synthase, and the terminal transaminase TyrB are suppressed by leucine. TyrB is subject to inhibition by the pathway's starting compound, 2-keto-isovalerate, and by one of its off-pathway products, tyrosine. One consequence of this inhibition by 2-keto-isovalerate is that in the absence of IlvE activity, mutations in earlier steps in the pathway cannot be compensated for by any alternate method of introducing 2-ketoisocaproate for conversion to leucine. PW000811MetabolicNAD biosynthesisNicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide.
Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners.
In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD.
In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD.
NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase.
As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan.
PW000829MetabolicNAD salvageEven though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+.
NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside.
Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide.
Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD.
Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD.
PW000830MetabolicPorphyrin metabolismThe metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter .
L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate.
This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane.
Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III.
Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I
Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III.
Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+
uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway.
Uroporphyrinogen III can be processed in anaerobic or aerobic condition.
Anaerobic:
Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX
Aerobic:
Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX.
The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway.
PW000936MetabolicSecondary Metabolite: Leucine biosynthesisLeucine biosynthesis involves a five-step conversion process starting with a 3-methyl-2-oxovaleric acid interacting with acetyl-CoA and a water molecule through a 2-isopropylmalate synthase resulting in Coenzyme A, hydrogen Ion and 2-isopropylmalic acid. The latter compound reacts with isopropylmalate isomerase which dehydrates the compound resulting in a Isopropylmaleate. This compound reacts with water through a isopropylmalate isomerase resulting in 3-isopropylmalate. This compound interacts with a NAD-driven D-malate / 3-isopropylmalate dehydrogenase results in 2-isopropyl-3-oxosuccinate. This compound interacts spontaneously with hydrogen resulting in the release of carbon dioxide and ketoleucine. Ketoleucine interacts in a reversible reaction with L-glutamic acid through a branched-chain amino-acid aminotransferase resulting in Oxoglutaric acid and L-leucine
Both the first enzyme in the pathway, 2-isopropylmalate synthase, and the terminal transaminase TyrB are suppressed by leucine. TyrB is subject to inhibition by the pathway's starting compound, 2-keto-isovalerate, and by one of its off-pathway products, tyrosine. One consequence of this inhibition by 2-keto-isovalerate is that in the absence of IlvE activity, mutations in earlier steps in the pathway cannot be compensated for by any alternate method of introducing 2-ketoisocaproate for conversion to leucine. PW000980MetabolicSecondary Metabolites: Histidine biosynthesisHistidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.PW000984MetabolicSecondary Metabolites: Valine and I-leucine biosynthesis from pyruvateThe biosynthesis of Valine and L-leucine from pyruvic acid starts with pyruvic acid interacting with a hydrogen ion through a acetolactate synthase / acetohydroxybutanoate synthase resulting in a release of a carbon dioxide, a (S)-2-acetolactate. The latter compound then interacts with a hydrogen ion through a NADPH-driven acetohydroxy acid isomeroreductase resulting in the release of a NADP, a (R) 2,3-dihydroxy-3-methylvalerate. The latter compound is then dehydrated by a dihydroxy acid dehydratase resulting in the release of a water molecule an 3-methyl-2-oxovaleric acid.
The 3-methyl-2-oxovaleric acid can produce an L-valine by interacting with a L-glutamic acid through a Valine Transaminase resulting in the release of a Oxoglutaric acid and a L-valine.
The 3-methyl-2-oxovaleric acid then interacts with an acetyl-CoA and a water molecule through a 2-isopropylmalate synthase resulting in the release of a hydrogen ion, a Coenzyme A and a 2-Isopropylmalic acid. The isopropylimalic acid is then hydrated by interacting with a isopropylmalate isomerase resulting in a 3-isopropylmalate. This compound then interacts with an NAD driven 3-isopropylmalate dehydrogenase resulting in a NADH, a hydrogen ion and a 2-isopropyl-3-oxosuccinate. The latter compound then interacts with hydrogen ion spontaneously resulting in a carbon dioxide and a ketoleucine. The ketoleucine then interacts with a L-glutamic acid through a branched-chain amino-acid aminotransferase resulting in the oxoglutaric acid and L-leucine.PW000978MetabolicSecondary Metabolites: cysteine biosynthesis from serineThe pathway starts with a 3-phosphoglyceric acid interacting with an NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in an NADH, a hydrogen ion and a phosphohydroxypyruvic acid. This compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in a oxoglutaric acid and a DL-D-phosphoserine. The latter compound then interacts with a water molecule through a phosphoserine phosphatase resulting in a phosphate and an L-serine. The L-serine interacts with an acetyl-coa through a serine acetyltransferase resulting in a release of a Coenzyme A and a O-Acetylserine. The O-acetylserine then interacts with a hydrogen sulfide through a O-acetylserine sulfhydrylase A resulting in an acetic acid, a hydrogen ion and an L-cysteinePW000977MetabolicSecondary Metabolites: enterobacterial common antigen biosynthesis
The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate.
Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc.
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane
Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW000959MetabolicValine Biosynthesis
The pathway of valine biosynthesis starts with pyruvic acid interacting with a hydrogen ion through a acetolactate synthase / acetohydroxybutanoate synthase or a acetohydroxybutanoate synthase / acetolactate synthase resulting in the release of carbon dioxide and (S)-2-acetolactate. The latter compound then interacts with a hydrogen ion through an NADPH driven
acetohydroxy acid isomeroreductase resulting in the release of a NADP and an (R) 2,3-dihydroxy-3-methylvalerate. The latter compound is then dehydrated by a
dihydroxy acid dehydratase resulting in the release of water and isovaleric acid. Isovaleric acid interacts with an L-glutamic acid through a Valine Transaminase resulting in a oxoglutaric acid and an L-valine.
L-valine is then transported into the periplasmic space through a L-valine efflux transporter.PW000812MetabolicVitamin B6 1430936196PW000891Metabolicarginine metabolismThe metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine.
L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion.
Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid.
L-arginine can be metabolized into succinic acid by two different sets of reactions:
1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and
a succinic acid. The succinic acid is then incorporated in the TCA cycle
2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cyclePW000790Metaboliccysteine biosynthesisThe pathway of cysteine biosynthesis is a two-step conversion starting from L-serine and yielding L-cysteine. L-serine biosynthesis is shown for context.
L-cysteine can also be synthesized from sulfate derivatives.
The process through L-serine involves a serine acetyltransferase that produces a O-acetylserine which reacts together with hydrogen sulfide through a cysteine synthase complex in order to produce L-cysteine and acetic acid.
Hydrogen sulfide is produced from a sulfate. Sulfate reacts with sulfate adenylyltransferase to produce adenosine phosphosulfate. This compound in turn is phosphorylated through a adenylyl-sulfate kinase into a phosphoadenosine phosphosulfate which in turn reacts with a phosphoadenosine phosphosulfate reductase to produce a sulfite. The sulfite reacts with a sulfite reductase to produce the hydrogen sulfide.
This pathway is regulated at the genetic level in its second step, wtih both cysteine synthase isozymes being under the positive control of the cysteine-responsive transcription factor CysB. It is also subject to very strong feedback inhibition of its first step by the final pathway product, cysteine.
Although two cysteine synthase isozymes exist, only cysteine synthase A (CysK) forms a complex with serine acetyltransferase. CysK is also the only one of the two cysteine synthases that is required for cell viability on cysteine-free medium.
Both steps in this pathway are reversible. Based on genetic and proteomic data, it appears that the cysteine synthases may actually act as a sulfur scavenging system during sulfur starvation, stripping sulfur off of L-cysteine, generating any number of variant amino acids in the process.PW000800Metabolichistidine biosynthesisHistidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.PW000810Metabolicinner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786Metabolicisoleucine biosynthesisIsoleucine biosynthesis begins with L-threonine from the threonine biosynthesis pathway. L-threonine interacts with a threonine dehydratase biosynthetic releasing water, a hydrogen ion and (2Z)-2-aminobut-2-enoate. This compound is isomerized into a 2-iminobutanoate which interacts with water and a hydrogen ion spontaneously, resulting in the release of ammonium and 2-ketobutyric acid. This compound reacts with pyruvic acid and hydrogen ion through an acetohydroxybutanoate synthase / acetolactate synthase 2 resulting in carbon dioxide and (S)-2-Aceto-2-hydroxybutanoic acid. The latter compound is reduced by an NADPH driven acetohydroxy acid isomeroreductase releasing NADP and acetohydroxy acid isomeroreductase. The latter compound is dehydrated by a dihydroxy acid dehydratase resulting in 3-methyl-2-oxovaleric acid.This compound reacts in a reversible reaction with L-glutamic acid through a Branched-chain-amino-acid aminotransferase resulting in oxoglutaric acid and L-isoleucine.
L-isoleucine can also be transported into the cytoplasm through two different methods: a branched chain amino acid ABC transporter or a
branched chain amino acid transporter BrnQ
y.
PW000818Metabolicornithine metabolism
In the ornithine biosynthesis pathway of E. coli, L-glutamate is acetylated to N-acetylglutamate by the enzyme N-acetylglutamate synthase, encoded by the argA gene. The acetyl donor for this reaction is acetyl-CoA. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NADPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. Ornithine interacts with hydrogen ion through a Ornithine decarboxylase resulting in a carbon dioxide release and a putrescine
Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
PW000791Metabolicpeptidoglycan biosynthesis IPeptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space.
The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.
PW000906Metabolicphenylalanine biosynthesisThe pathways of biosynthesis of phenylalaline and tyrosine are intimately connected. First step of both pathways is the conversion of chorismate to prephenate, the third step of both is the conversion of a ketoacid to the aminoacid through transamination. The two pathways differ only in the second step of their three-step reaction sequences: In the case of phenylalanine biosynthesis, a dehydratase converts prephenate to phenylpyruvate(reaction occurs slowly in the absence of enzymic activity); in the case of tyrosine biosynthesis, a dehydrogenase converts prephenate to p-hydroxyphenylpyruvate. Also in both pathways the first two steps are catalyzed by two distinc active sites on a single protein. Thus the first step of each pathway can be catalyzed by two enzyme: those associated with both the phenylalanine specific dehydratase and the tyrosine specific dehydrogenase. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosinePW000807Metabolicproline metabolism
The biosynthesis of L-proline in E. coli involves L-glutamic acid being phosphorylated through an ATP driven glutamate 5-kinase resulting in a L-glutamic acid 5-phosphate. This compound is then reduced through a NADPH driven gamma glutamyl phosphate reductase resulting in the release of a phosphate, a NADP and a L-glutamic gamma-semialdehyde.
L-glutamic gamma-semialdehyde is dehydrated spontaneously, resulting in a release of water,hydrogen ion and 1-Pyrroline-5-carboxylic acid. The latter compound is reduced by an NADPH driven pyrroline-5-carboxylate reductase which is subsequently reduced to L-proline. L-proline works as a repressor of the pyrroline-5-carboxylate reductase enzyme and glutamate 5-kinase.
In E. coli, the biosynthesis of L-proline from L-glutamate is governed by three genetic loci namely proB, proA and proC. The first reaction in the pathway is catalyzed by γ-glutamyl kinase, encoded by proB . The second reaction, NADPH-dependent reduction of γ-glutamyl phosphate to glutamate-5-semialdehyde, in the pathway is catalyzed by glutamate-5-semialdehyde dehydrogenase, encoded by proA . These two enzymes aggregate into a multimeric bi-functional enzyme complex known as γ-glutamyl kinase-GP-reductase multienzyme complex. It is believed that the complex formation serves to protect the highly labile glutamyl phosphate from the hostile nucleophilic and aqueous environment found in the cell . The final step in the pathway, the reduction of pyrroline 5-carboxylate to L-proline, is catalyzed by an NADPH-dependent pyrroline-5-carboxylate reductase encoded by proC .
Proline is metabolized by being converted back to L-glutamate, which is further degraded to α-ketoglutarate, an intermediate of the TCA cycle. Curiously, L-glutamate, the obligate intermediate of the proline degradation pathway, cannot itself serve as a total source of carbon and energy for E. coli, because glutamate transport supplies exogenous glutamate at an inadequate rate.
The proces by which proline is turned into L-glutamate starts with L-proline interacting with ubiquinone through a bifunctional protein putA resulting in an ubiquinol, a hydrogen ion and a 1-pyrroline-5-carboxylic acid. The latter compound is then hydrated spontaneously resulting in a L-glutamic gamma-semialdehyde. This compound is then processed by interacting with water through an NAD driven bifunctional protein putA resulting in a hydrogen ion, NADH and L-glutamic acid.PW000794Metabolicpurine nucleotides de novo biosynthesisThe biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a
amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven
phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide.The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid.
Inosinic acid can be metabolized to produce dGTP and dATP three different methods each.
dGTP:
Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways:
1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP
2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP.
3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP.
dATP:
Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways:
1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP
2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP
3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP
PW000910Metabolicpurine nucleotides de novo biosynthesis 1435709748PW000960Metabolicserine biosynthesis and metabolismSerine biosynthesis is a major metabolic pathway in E. coli. Its end product, serine, is not only used in protein synthesis, but also as a precursor for the biosynthesis of glycine, cysteine, tryptophan, and phospholipids. In addition, it directly or indirectly serves as a source of one-carbon units for the biosynthesis of various compounds.
The biosynthesis of serine starts with 3-phosphoglyceric acid being metabolized by a NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in the release of a NADH, a hydrogen ion and a phosphohydroxypyruvic acid. The latter compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in oxoglutaric acid and DL-D-phosphoserine.
The DL-D-phosphoserine can also be imported into the cytoplasm through a phosphonate ABC transporter. The DL-D-phosphoserine is dephosphorylated by interacting with a water molecule through a phosphoserine phosphatase resulting in the release of a phosphate and an L-serine
L-serine is then metabolized by being dehydrated through either a L-serine dehydratase 2 or a L-serine dehydratase 1 resulting in the release of a water molecule, a hydrogen ion and a 2-aminoacrylic acid. The latter compound is an isomer of a 2-iminopropanoate which reacts spontaneously with a water molecule and a hydrogen ion resulting in the release of Ammonium and pyruvic acid. Pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an acetyl-CoA.
PW000809MetabolictRNA Charging 2This pathway groups together all E. coli tRNA charging reactions.PW000803MetabolictRNA chargingThis pathway groups together all E. coli tRNA charging reactions.PW000799Metabolicthreonine biosynthesisThe biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817Metabolictyrosine biosynthesisThe pathways of biosynthesis of phenylalaline and tyrosine are intimately connected. First step of both pathways is the conversion of chorismate to prephenate, the third step of both is the conversion of a ketoacid to the aminoacid through transamination. The two pathways differ only in the second step of their three-step reaction sequences: In the case of phenylalanine biosynthesi a dehydratase converts prephenate to phenylpyruvate(reaction occurs slowly in the absence of enzymic activity); in the case of tyrosine biosynthesis, a dehydrogenase converts prephenate to p-hydroxyphenylpyruvate. Also in both pathways the first two steps are catalyzed by two distinc active sites on a single protein. Thus the first step of each pathway can be catalyzed by two enzyme: those associated with both the phenylalanine specific dehydratase and the tyrosine specific dehydrogenase. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosinePW000806Metabolicglutathione metabolism IIThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene through a glutathione S-transferase
PW001927Metaboliclipopolysaccharide biosynthesis IIE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA. A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and CMP-3-deoxy-α-D-manno-octulosonate. CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound can either interact with a phosphoethanolamine resulting in a 1,2-diacyl-sn-glycerol and a phosphoethanolamine-Kdo2-lipid A which can be exported outside the cell, or it can interact with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core. A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter. The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface.PW001905Metabolictryptophan metabolism IIThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoAPW001916Metabolicglutathione metabolism IIIThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW002018MetabolicThiamin diphosphate biosynthesisPW002028Metabolic4-aminobutanoate degradation IE. coli can utilize putrescine as the sole source of carbon and nitrogen. The enzymes of the putrescine degradation II pathway are inducible by extracellular putrescine, leading to the production of GABA. Both enzymes of this pathway are inducible by putrescine in E. coli.
This variant of the pathway includes a 2-oxoglutarate-dependent 4-aminobutyrate transaminase and an NAD+-dependent dehydrogenase. This combination of enzymes has been documented in bacteria and animals and in some plants.
Regarding the hydrogenase, NAD-specific variants have been studied from many bacteria, plant and animals.PW002068MetabolicHydrogen Sulfide Biosynthesis IIt has long been known that many bacteria are able to produce hydrogen sulfide [Barrett87]. However, the physiological role of H2S in nonsulfur bacteria was unknown. A recent report has now shown that production of H2S serves to defend cells from antibiotics by mitigating oxidative stress.
This pathway is one of two pathways for hydrogen sulfide biosynthesis. Neither of the two activities have been shown biochemically for the E. coli enzymes. The function of AspC as a cysteine transaminase is hypothesized based on sequence similarity to mammalian enzymes. The function of SseA was determined based on the phenotype of an sseA null mutant, which does not produce hydrogen sulfide.PW002066MetabolicPutrescine Degradation IISeveral metabolic pathways for putrescine degradation as a source of nitrogen for E. coli K-12 are known. The first putrescine degradation pathway was found in in 1985. That pathway is dedicated to the degradation of intracellular putrescine. A second pathway was found in E. coli K-12 twenty years later. This pathway seems to be dedicated to the degradation of extracellular putrescine.
The pathway was discovered following the discovery of a cluster of seven unassigned genes on the E. coli K-12 chromosome. In addition to a putrescine transporter, encoded by the puuP gene, the cluster contains four genes that encode the enzymes involved in this pathway, and two additional genes (puuE and puuR) that encode an enzyme involved in the catabolism of GABA (see superpathway of 4-aminobutanoate degradation) and a regulator.
In this pathway, putrescine is γ-glutamylated at the expense of an ATP molecule. The resulting γ-glutamyl-putrescine is oxidized to γ-glutamyl-γ-aminobutyraldehyde, which is then dehydrogenated into 4-(glutamylamino) butanoate. In the last step, the γ-glutamyl group is removed by hydrolysis, generating 4-aminobutyrate.
The key difference between this pathway and putrescine degradation I is the γ-glutamylation of putrescine. In the other pathway, putrescine is degraded directly to 4-amino-butanal.
Wild type E. coli cells are unable to utilize putrescine as the sole source of carbon at temperatures above 30°C. It is possible to select for mutants that possess this ability; these mutants contain elevated levels of the enzymes in this pathway. (EcoCyc)PW002054MetabolicSecondary Metabolites: enterobacterial common antigen biosynthesis 2The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW002045MetabolicSecondary Metabolites: enterobacterial common antigen biosynthesis 3The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW002046Metaboliclipopolysaccharide biosynthesis IIIE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound can either react with a palmitoleoyl-acp through a palmitoleoyl acyltransferase resulting in the release of a holo-acyl carriere protein and a Kdo2-palmitoleoyl-lipid IVa which in turn reacts with a myristoyl-acp through a myristoyl-acp dependent acyltransferase resulting in a release of a holo-acp and a Kdo2-lipid A, cold adapted, or it can interact with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW002059Metabolicpeptidoglycan biosynthesis I 2Peptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space. The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.PW002062Metabolicpolymyxin resistanceUDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate.
The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid APW002052Metabolicpurine nucleotides de novo biosynthesis 2The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide(5-Phosphoribosyl-5-carboxyaminoimidazole).The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATPPW002033MetabolicO-antigen building blocks biosynthesisLipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A; the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as O-antigen.
E. coli K12 is capable of producing an O-antigen when all the rfb genes are intact. The O-antigen is part of the lipopolysaccharide and is attached to the lipid A-core component, which is separately synthesized. The O-antigen is a repeat unit composed of four sugars: glucose, N-acetylglucosamine, galactose and rhamnose.
This pathway depicts the synthesis of three of these sugars. UDP-galactose is transformed from its pyranose form to its furanose form. dTTP glucose-1-phosphate is derivatized to dTDP-rhamnose. Fructose-6-phosphate gains an amino group, incorporates an acetate moiety and then acquires a nucleoside diphosphate resulting in UDP-N-acetyl-D-glucosamine.(EcoCyc)PW002089Metabolicisoleucine biosynthesis I (from threonine)ILEUSYN-PWYornithine biosynthesisGLUTORN-PWYasparagine biosynthesis IASPARAGINE-BIOSYNTHESISNAD salvage pathway IPYRIDNUCSAL-PWYtRNA chargingTRNA-CHARGING-PWYtetrapyrrole biosynthesis IPWY-5188NAD biosynthesis I (from aspartate)PYRIDNUCSYN-PWYarginine biosynthesis IARGSYN-PWYguanosine nucleotides <i>de novo</i> biosynthesisPWY-6125formylTHF biosynthesis I1CMET2-PWYglutamate biosynthesis IIIGLUTSYNIII-PWYglutamine degradation IGLUTAMINDEG-PWYarginine degradation II (AST pathway)AST-PWYglutamate degradation IIGLUTDEG-PWYglutamine biosynthesis IGLNSYN-PWYNitrogen Regulation Two-Component SystemNRI-PWYpyrimidine ribonucleotides interconversionPWY-5687-1folate polyglutamylationPWY-2161glutathione biosynthesisGLUTATHIONESYN-PWYsuperpathway of 5-aminoimidazole ribonucleotide biosynthesisPWY-62775-aminoimidazole ribonucleotide biosynthesis IPWY-61215-aminoimidazole ribonucleotide biosynthesis IIPWY-6122UDP-<i>N</i>-acetyl-D-glucosamine biosynthesis IUDPNAGSYN-PWYpolymyxin resistancePWY0-1338uridine-5'-phosphate biosynthesisPWY-5686glutamate biosynthesis IGLUTSYN-PWYproline degradationPROUT-PWYhistidine biosynthesisHISTSYN-PWYalanine biosynthesis IIALANINE-SYN2-PWYaspartate biosynthesisASPARTATESYN-PWYisoleucine biosynthesis I (from threonine)LEUSYN-PWYalanine biosynthesis IALANINE-VALINESYN-PWYvaline biosynthesisVALSYN-PWYhydrogen sulfide biosynthesisPWY0-15344-aminobutyrate degradation IPWY-65354-aminobutyrate degradation IIPWY-6537<i>p</i>-aminobenzoate biosynthesisPWY-6543phenylalanine biosynthesis IPHESYNhomoserine biosynthesisSERSYN-PWYpyridoxal 5'-phosphate biosynthesis IPYRIDOXSYN-PWYputrescine degradation IPUTDEG-PWYenterobacterial common antigen biosynthesisECASYN-PWYlysine biosynthesis IDAPLYSINESYN-PWYtyrosine biosynthesis ITYRSYNproline biosynthesis IPROSYN-PWYputrescine degradation IIPWY0-1221glutamate dependent acid resistancePWY0-1305tryptophan biosynthesisTRPSYN-PWYUDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing)PWY-6387tetrahydrofolate biosynthesisPWY-6614Specdb::CMs366Specdb::CMs367Specdb::CMs368Specdb::CMs1228Specdb::CMs1296Specdb::CMs2359Specdb::CMs30048Specdb::CMs30367Specdb::CMs30552Specdb::CMs30735Specdb::CMs30790Specdb::CMs31022Specdb::CMs31023Specdb::CMs37320Specdb::CMs146692Specdb::CMs1051565Specdb::CMs1051566Specdb::CMs1051568Specdb::CMs1051570Specdb::CMs1051572Specdb::CMs1051574Specdb::CMs1051575Specdb::CMs1051577Specdb::CMs1051579Specdb::CMs1051581Specdb::NmrOneD1109Specdb::NmrOneD1168Specdb::NmrOneD142550Specdb::NmrOneD142551Specdb::NmrOneD142552Specdb::NmrOneD142553Specdb::NmrOneD142554Specdb::NmrOneD142555Specdb::NmrOneD142556Specdb::NmrOneD142557Specdb::NmrOneD142558Specdb::NmrOneD142559Specdb::NmrOneD142560Specdb::NmrOneD142561Specdb::NmrOneD142562Specdb::NmrOneD142563Specdb::NmrOneD142564Specdb::NmrOneD142565Specdb::NmrOneD142566Specdb::NmrOneD142567Specdb::NmrOneD142568Specdb::NmrOneD142569Specdb::NmrOneD166499Specdb::NmrOneD166550Specdb::NmrOneD166566Specdb::MsMs221Specdb::MsMs222Specdb::MsMs223Specdb::MsMs3055Specdb::MsMs3056Specdb::MsMs3057Specdb::MsMs3058Specdb::MsMs3059Specdb::MsMs3060Specdb::MsMs3061Specdb::MsMs3062Specdb::MsMs3063Specdb::MsMs3064Specdb::MsMs3065Specdb::MsMs3066Specdb::MsMs3067Specdb::MsMs3068Specdb::MsMs3069Specdb::MsMs3070Specdb::MsMs3071Specdb::MsMs3072Specdb::MsMs3073Specdb::MsMs3074Specdb::MsMs3075Specdb::MsMs3076Specdb::NmrTwoD969Specdb::NmrTwoD1168HMDB001483303230572C0002516015GLTGLU_LFZW_DHE2Glutamic_acidKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72.18402659van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). 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(1955), 591 117-34.http://hmdb.ca/system/metabolites/msds/000/000/101/original/HMDB00148.pdf?1358894673NADP-specific glutamate dehydrogenaseP00370DHE4_ECOLIgdhAhttp://ecmdb.ca/proteins/P00370.xmlAspartate aminotransferaseP00509AAT_ECOLIaspChttp://ecmdb.ca/proteins/P00509.xmlL-asparaginase 2P00805ASPG2_ECOLIansBhttp://ecmdb.ca/proteins/P00805.xmlAnthranilate synthase component 1P00895TRPE_ECOLItrpEhttp://ecmdb.ca/proteins/P00895.xmlPara-aminobenzoate synthase glutamine amidotransferase component IIP00903PABA_ECOLIpabAhttp://ecmdb.ca/proteins/P00903.xmlAnthranilate synthase component IIP00904TRPG_ECOLItrpDhttp://ecmdb.ca/proteins/P00904.xmlCarbamoyl-phosphate synthase large chainP00968CARB_ECOLIcarBhttp://ecmdb.ca/proteins/P00968.xmlGMP synthase [glutamine-hydrolyzing]P04079GUAA_ECOLIguaAhttp://ecmdb.ca/proteins/P04079.xmlAromatic-amino-acid aminotransferaseP04693TYRB_ECOLItyrBhttp://ecmdb.ca/proteins/P04693.xmlGlutamyl-tRNA synthetaseP04805SYE_ECOLIgltXhttp://ecmdb.ca/proteins/P04805.xmlPara-aminobenzoate synthase component 1P05041PABB_ECOLIpabBhttp://ecmdb.ca/proteins/P05041.xmlHistidinol-phosphate aminotransferaseP06986HIS8_ECOLIhisChttp://ecmdb.ca/proteins/P06986.xmlBifunctional protein folCP08192FOLC_ECOLIfolChttp://ecmdb.ca/proteins/P08192.xmlBifunctional protein putAP09546PUTA_ECOLIputAhttp://ecmdb.ca/proteins/P09546.xmlGlutamate synthase [NADPH] large chainP09831GLTB_ECOLIgltBhttp://ecmdb.ca/proteins/P09831.xmlGlutamate synthase [NADPH] small chainP09832GLTD_ECOLIgltDhttp://ecmdb.ca/proteins/P09832.xmlAmino-acid acetyltransferaseP0A6C5ARGA_ECOLIargAhttp://ecmdb.ca/proteins/P0A6C5.xmlCarbamoyl-phosphate synthase small chainP0A6F1CARA_ECOLIcarAhttp://ecmdb.ca/proteins/P0A6F1.xmlGlutaminase 2P0A6W0GLSA2_ECOLIglsA2http://ecmdb.ca/proteins/P0A6W0.xmlGlutamate--cysteine ligaseP0A6W9GSH1_ECOLIgshAhttp://ecmdb.ca/proteins/P0A6W9.xmlGlutamate 5-kinaseP0A7B5PROB_ECOLIproBhttp://ecmdb.ca/proteins/P0A7B5.xmlCTP synthaseP0A7E5PYRG_ECOLIpyrGhttp://ecmdb.ca/proteins/P0A7E5.xmlGlutamine synthetaseP0A9C5GLNA_ECOLIglnAhttp://ecmdb.ca/proteins/P0A9C5.xmlAmidophosphoribosyltransferaseP0AG16PUR1_ECOLIpurFhttp://ecmdb.ca/proteins/P0AG16.xmlPhosphoribosylformylglycinamidine synthaseP15254PUR4_ECOLIpurLhttp://ecmdb.ca/proteins/P15254.xmlAminoacyl-histidine dipeptidaseP15288PEPD_ECOLIpepDhttp://ecmdb.ca/proteins/P15288.xmlGlucosamine--fructose-6-phosphate aminotransferase [isomerizing]P17169GLMS_ECOLIglmShttp://ecmdb.ca/proteins/P17169.xmlAcetylornithine/succinyldiaminopimelate aminotransferaseP18335ARGD_ECOLIargDhttp://ecmdb.ca/proteins/P18335.xmlNH(3)-dependent NAD(+) synthetaseP18843NADE_ECOLInadEhttp://ecmdb.ca/proteins/P18843.xmlGamma-glutamyltranspeptidaseP18956GGT_ECOLIggthttp://ecmdb.ca/proteins/P18956.xmlAsparagine synthetase B [glutamine-hydrolyzing]P22106ASNB_ECOLIasnBhttp://ecmdb.ca/proteins/P22106.xml4-aminobutyrate aminotransferaseP22256GABT_ECOLIgabThttp://ecmdb.ca/proteins/P22256.xmlGlutamate racemaseP22634MURI_ECOLImurIhttp://ecmdb.ca/proteins/P22634.xmlPhosphoserine aminotransferaseP23721SERC_ECOLIserChttp://ecmdb.ca/proteins/P23721.xmlAcetylornithine deacetylaseP23908ARGE_ECOLIargEhttp://ecmdb.ca/proteins/P23908.xmlPutrescine aminotransferaseP42588PAT_ECOLIpatAhttp://ecmdb.ca/proteins/P42588.xml4-aminobutyrate aminotransferase_P50457PUUE_ECOLIpuuEhttp://ecmdb.ca/proteins/P50457.xmlGlutamate decarboxylase alphaP69908DCEA_ECOLIgadAhttp://ecmdb.ca/proteins/P69908.xmlGlutamate decarboxylase betaP69910DCEB_ECOLIgadBhttp://ecmdb.ca/proteins/P69910.xmlGamma-glutamyl-gamma-aminobutyrate hydrolaseP76038PUUD_ECOLIpuuDhttp://ecmdb.ca/proteins/P76038.xmlSuccinylglutamate desuccinylaseP76215ASTE_ECOLIastEhttp://ecmdb.ca/proteins/P76215.xmlGlutaminase 1P77454GLSA1_ECOLIglsA1http://ecmdb.ca/proteins/P77454.xmlSuccinylornithine transaminaseP77581ASTC_ECOLIastChttp://ecmdb.ca/proteins/P77581.xmlUDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferaseP77690ARNB_ECOLIarnBhttp://ecmdb.ca/proteins/P77690.xmlGamma-glutamylputrescine synthetaseP78061PUUA_ECOLIpuuAhttp://ecmdb.ca/proteins/P78061.xmlGlutamate/aspartate transport system permease protein gltJP0AER3GLTJ_ECOLIgltJhttp://ecmdb.ca/proteins/P0AER3.xmlGlutamate/aspartate transport system permease protein gltKP0AER5GLTK_ECOLIgltKhttp://ecmdb.ca/proteins/P0AER5.xmlImidazole glycerol phosphate synthase subunit hisHP60595HIS5_ECOLIhisHhttp://ecmdb.ca/proteins/P60595.xmlUncharacterized aminotransferase yfbQP0A959YFBQ_ECOLIyfbQhttp://ecmdb.ca/proteins/P0A959.xmlBranched-chain-amino-acid aminotransferaseP0AB80ILVE_ECOLIilvEhttp://ecmdb.ca/proteins/P0AB80.xmlLipopolysaccharide biosynthesis protein rffAP27833RFFA_ECOLIrffAhttp://ecmdb.ca/proteins/P27833.xmlImidazole glycerol phosphate synthase subunit hisFP60664HIS6_ECOLIhisFhttp://ecmdb.ca/proteins/P60664.xmlGlutamate/aspartate transport ATP-binding protein gltLP0AAG3GLTL_ECOLIgltLhttp://ecmdb.ca/proteins/P0AAG3.xmlGlutamate/aspartate periplasmic-binding proteinP37902GLTI_ECOLIgltIhttp://ecmdb.ca/proteins/P37902.xmlUncharacterized aminotransferase yfdZP77434YFDZ_ECOLIyfdZhttp://ecmdb.ca/proteins/P77434.xmlUncharacterized amino-acid ABC transporter ATP-binding protein yecCP37774YECC_ECOLIyecChttp://ecmdb.ca/proteins/P37774.xmlInner membrane amino-acid ABC transporter permease protein yecSP0AFT2YECS_ECOLIyecShttp://ecmdb.ca/proteins/P0AFT2.xmlGlutamate/aspartate transport system permease protein gltJP0AER3GLTJ_ECOLIgltJhttp://ecmdb.ca/proteins/P0AER3.xmlGlutamate/aspartate transport system permease protein gltKP0AER5GLTK_ECOLIgltKhttp://ecmdb.ca/proteins/P0AER5.xmlSodium/glutamate symport carrier proteinP0AER8GLTS_ECOLIgltShttp://ecmdb.ca/proteins/P0AER8.xmlProton glutamate symport proteinP21345GLTP_ECOLIgltPhttp://ecmdb.ca/proteins/P21345.xmlProbable glutamate/gamma-aminobutyrate antiporterP63235GADC_ECOLIgadChttp://ecmdb.ca/proteins/P63235.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlGlutamate/aspartate transport ATP-binding protein gltLP0AAG3GLTL_ECOLIgltLhttp://ecmdb.ca/proteins/P0AAG3.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlGlutamate/aspartate periplasmic-binding proteinP37902GLTI_ECOLIgltIhttp://ecmdb.ca/proteins/P37902.xml2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + PhosphateR00575CARBPSYN-RXNAdenosine triphosphate + Water + L-Glutamate > ADP + L-Glutamate + Hydrogen ion + PhosphateABC-13-RXNAdenosine triphosphate + Water + L-Glutamate > ADP + L-Glutamate + Hydrogen ion + PhosphateABC-13-RXNChorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidR00986ANTHRANSYN-RXNN-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-GlutamateR02283L-Glutamine + Water > L-Glutamate + AmmoniumL-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ionalpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidR00258gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehydeR01648alpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPR00114Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-GlutamateR01716PABASYN-RXNL-Glutamate + Hydrogen ion <> gamma-Aminobutyric acid + Carbon dioxideR00261GLUTDECARBOX-RXNKetoleucine + L-Glutamate > alpha-Ketoglutarate + L-LeucineAdenosine triphosphate + L-Glutamate + Ammonium > ADP + L-Glutamine + Hydrogen ion + Phosphatealpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acidR00694alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-GlutamateR00734L-Alanine-L-glutamate + Water > L-Alanine + L-GlutamateAdenosine triphosphate + L-Glutamate > ADP + L-Glutamic acid 5-phosphateGLUTKIN-RXNL-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + PyrophosphateR00578ASNSYNB-RXNL-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonineR05085Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + PhosphoserineR04173alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acidR00355L-D-1-Pyrroline-5-carboxylic acid + 2 Water + NAD > L-Glutamate + Hydrogen ion + NADHR00707PYRROLINECARBDEHYDROG-RXNAdenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + PhosphateR07414RXN0-39014-(Glutamylamino) butanoate + Water <> gamma-Aminobutyric acid + L-GlutamateR07419RXN0-3942Water + N-Succinyl-L-glutamate <> L-Glutamate + Succinic acidR00411alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehydeR04217L-Glutamate + Water + NADP <> alpha-Ketoglutarate + Hydrogen ion + NADPH + AmmoniumL-Glutamate + Imidazole acetol-phosphate <> alpha-Ketoglutarate + Histidinol phosphateR03243L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinoseR07659L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate + 5-PhosphoribosylamineR01072PRPPAMIDOTRANS-RXNAdenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Dihydrofolic acid + Hydrogen ion + PhosphateR02237DIHYDROFOLATESYNTH-RXNAdenosine triphosphate + L-Glutamate + tRNA (Glu) > Adenosine monophosphate + L-Glutamyl-tRNA(Glu) + PyrophosphateAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + PyrophosphateR01231GMP-SYN-GLUT-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateR04463FGAMSYN-RXNAdenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + PhosphateR00894GLUTCYSLIG-RXNAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateR00573CTPSYN-RXNAcetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acidR00259alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-GlutamateR01155alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelateR04475Glutathione + Water > Cysteinylglycine + L-GlutamateR00494Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-GlutamateR00768L-GLN-FRUCT-6-P-AMINOTRANS-RXNalpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-GlutamateR02199alpha-Ketoglutarate + L-Valine <> alpha-Ketoisovaleric acid + L-GlutamateR012144,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-FucosamineD-Glutamic acid <> L-GlutamateR00260GLUTRACE-RXN2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ionR000932 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ionR00114Adenosine triphosphate + L-Glutamate <> ADP + L-Glutamyl 5-phosphate + L-Glutamic acid 5-phosphateR00239L-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ionR00243L-Glutamic-gamma-semialdehyde + NAD + Water <> L-Glutamate + NADH + Hydrogen ionR00245L-Glutamate + NADP + Water <> alpha-Ketoglutarate + Ammonia + NADPH + Hydrogen ionR00248Adenosine triphosphate + L-Glutamate + Ammonia <> ADP + Phosphate + L-GlutamineR00253GLUTAMINESYN-RXNL-Glutamine + Water <> L-Glutamate + AmmoniaR00256GLUTAMIN-RXNAcetyl-CoA + L-Glutamate <> Coenzyme A + N-Acetyl-L-alanineR00259L-Glutamate <> D-Glutamic acidR00260GLUTRACE-RXNL-Glutamate <> gamma-Aminobutyric acid + Carbon dioxideR00261Glutathione + Water <> Cysteinylglycine + L-GlutamateR00494Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water <> ADP + Phosphate + Cytidine triphosphate + L-GlutamateR005732 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water <>2 ADP + Phosphate + L-Glutamate + CarbamoylphosphateR00575Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-GlutamateR00578L-D-1-Pyrroline-5-carboxylic acid + NAD + 2 Water <> L-Glutamate + NADH + Hydrogen ionR00707L-D-1-Pyrroline-5-carboxylic acid + NADP + 2 Water <> L-Glutamate + NADPH + Hydrogen ionR00708Adenosine triphosphate + L-Glutamate + L-Cysteine <> ADP + Phosphate + gamma-GlutamylcysteineR00894beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-GlutamateR00908Adenosine triphosphate + Tetrahydrofolic acid + L-Glutamate <> ADP + Phosphate + Tetrahydrofolyl-[Glu](2)R00942Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR009865-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + WaterR01072L-Leucine + alpha-Ketoglutarate <> 4-Methyl-2-oxopentanoate + L-Glutamate + KetoleucineR01090Putrescine + alpha-Ketoglutarate <> 4-Aminobutyraldehyde + L-GlutamateR01155Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-GlutamateR01231Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Phosphate + Dihydrofolic acidR02237Cysteic acid + alpha-Ketoglutarate <> 3-Sulfopyruvic acid + L-GlutamateR024333-Sulfinoalanine + alpha-Ketoglutarate <> 3-Sulfinylpyruvic acid + L-GlutamateR02619Histidinol phosphate + alpha-Ketoglutarate <> Imidazole acetol-phosphate + L-GlutamateR03243R-S-Glutathione + Water <> R-S-Cysteinylglycine + L-GlutamateR039163-Cyano-L-alanine + L-Glutamate <> gamma-Glutamyl-beta-cyanoalanine + WaterR03970beta-Aminopropionitrile + L-Glutamate <> gamma-Glutamyl-beta-aminopropiononitrile + WaterR03971Phosphoserine + alpha-Ketoglutarate <> Phosphohydroxypyruvic acid + L-GlutamateR04173(S)-b-aminoisobutyric acid + alpha-Ketoglutarate <> (S)-Methylmalonic acid semialdehyde + L-GlutamateR04188Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateR04463FGAMSYN-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-GlutamateR04558GLUTAMIDOTRANS-RXNL-erythro-4-Hydroxyglutamate + alpha-Ketoglutarate <> D-4-Hydroxy-2-oxoglutarate + L-GlutamateR05052O-Phospho-4-hydroxy-L-threonine + alpha-Ketoglutarate <> 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-GlutamateR05085tRNA(Glu) + L-Glutamate + Adenosine triphosphate + tRNA(Glu) <> L-Glutamyl-tRNA(Glu) + Pyrophosphate + Adenosine monophosphate + L-Glutamyl-tRNA(Glu)R055782-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-KetoglutarateR07396Adenosine triphosphate + L-Glutamate + Putrescine <> ADP + Phosphate + gamma-Glutamyl-L-putrescineR074146-Thioxanthine 5'-monophosphate + Adenosine triphosphate + L-Glutamine + Water <> 6-Thioguanosine monophosphate + Adenosine monophosphate + Pyrophosphate + L-GlutamateR08244Hydrogen ion + L-Glutamate + Adenosine triphosphate + NADPH > ADP + L-Glutamic-gamma-semialdehyde + NADP + PhosphatePROLINE-MULTIOxoglutaric acid + kynurenine L-Glutamate + 4-(2-aminophenyl)-2,4-dioxobutanoate2.6.1.7-RXNAdenosine triphosphate + L-Glutamate + Water > ADP + Phosphate + L-Glutamate + Hydrogen ionABC-13-RXNAdenosine triphosphate + L-Glutamate + Water > ADP + Phosphate + L-Glutamate + Hydrogen ionABC-13-RXNN-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-GlutamateACETYLORNTRANSAM-RXNOxoglutaric acid + L-Alanine <> L-Glutamate + Pyruvic acidALANINE-AMINOTRANSFERASE-RXNChorismate + L-Glutamine > Hydrogen ion + 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR00986ANTHRANSYN-RXNL-Aspartic acid + Oxoglutaric acid <> Oxalacetic acid + L-GlutamateASPAMINOTRANS-RXNL-Isoleucine + Oxoglutaric acid <> 3-Methyl-2-oxovaleric acid + L-GlutamateBRANCHED-CHAINAMINOTRANSFERILEU-RXNL-Leucine + Oxoglutaric acid <> Ketoleucine + L-GlutamateBRANCHED-CHAINAMINOTRANSFERLEU-RXNL-Valine + Oxoglutaric acid <> alpha-Ketoisovaleric acid + L-GlutamateBRANCHED-CHAINAMINOTRANSFERVAL-RXNAdenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water > Hydrogen ion + Carbamoylphosphate + L-Glutamate + Phosphate + ADPCARBPSYN-RXNAdenosine triphosphate + Uridine triphosphate + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Cytidine triphosphate + L-GlutamateCTPSYN-RXNOxoglutaric acid + L-Cysteine > L-Glutamate + 3-Mercaptopyruvic acidCYSTEINE-AMINOTRANSFERASE-RXNan aliphatic α,ω-diamine + Oxoglutaric acid <> an aliphatic ω-aminoaldehyde + L-GlutamateDIAMTRANSAM-RXNL-Glutamate + 7,8-Dihydropteroic acid + Adenosine triphosphate > Hydrogen ion + Dihydrofolic acid + Phosphate + ADPDIHYDROFOLATESYNTH-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateFGAMSYN-RXNa tetrahydrofolate-glutamate + L-Glutamate + Adenosine triphosphate > a tetrahydrofolate-glutamate + Phosphate + ADPFOLYLPOLYGLUTAMATESYNTH-RXNan <i>N</i><sup>10</sup>-formyl-tetrahydrofolate + L-Glutamate + Adenosine triphosphate > an <i>N</i><sup>10</sup>-formyl-tetrahydrofolate + ADP + PhosphateFORMYLTHFGLUSYNTH-RXNOxoglutaric acid + gamma-Aminobutyric acid <> L-Glutamate + Succinic acid semialdehydeGABATRANSAM-RXNL-Glutamate + NADP < Hydrogen ion + L-Glutamine + Oxoglutaric acid + NADPHGLUTAMATESYN-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICARGLUTAMIDOTRANS-RXNL-Glutamine + Water > Hydrogen ion + L-Glutamate + AmmoniaGLUTAMIN-RXNAmmonia + L-Glutamate + Adenosine triphosphate > L-Glutamine + ADP + PhosphateGLUTAMINESYN-RXNL-Cysteine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamylcysteine + Phosphate + ADPGLUTCYSLIG-RXNHydrogen ion + L-Glutamate > Carbon dioxide + gamma-Aminobutyric acidGLUTDECARBOX-RXNL-Glutamate + Water + NADP <> Hydrogen ion + Oxoglutaric acid + Ammonia + NADPHGLUTDEHYD-RXNWater + L-Glutamine + Xanthylic acid + Adenosine triphosphate > Hydrogen ion + L-Glutamate + Guanosine monophosphate + Pyrophosphate + Adenosine monophosphateR01231GMP-SYN-GLUT-RXNImidazole acetol-phosphate + L-Glutamate <> Histidinol phosphate + Oxoglutaric acidHISTAMINOTRANS-RXNFructose 6-phosphate + L-Glutamine > Glucosamine 6-phosphate + L-GlutamateL-GLN-FRUCT-6-P-AMINOTRANS-RXNL-Glutamate + Acetyl-CoA <> Hydrogen ion + <i>N</i>-acetyl-L-glutamate + Coenzyme AN-ACETYLTRANSFER-RXNAdenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD + L-GlutamateNAD-SYNTH-GLN-RXNPhenylpyruvic acid + L-Glutamate <> L-Phenylalanine + Oxoglutaric acidPHEAMINOTRANS-RXN5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + WaterR01072PRPPAMIDOTRANS-RXNPhosphoserine + Oxoglutaric acid <> Phosphohydroxypyruvic acid + L-GlutamatePSERTRANSAM-RXN2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acidPSERTRANSAMPYR-RXNPutrescine + Oxoglutaric acid <> 4-Aminobutyraldehyde + L-GlutamatePUTTRANSAM-RXNL-D-1-Pyrroline-5-carboxylic acid + NAD + Water > Hydrogen ion + L-Glutamate + NADHPYRROLINECARBDEHYDROG-RXN4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate <> dTDP-D-Fucosamine + Oxoglutaric acidRFFTRANS-RXNUridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + Oxoglutaric acid <> UDP-4-Keto-pyranose + L-GlutamateRXN0-1863a 5,10-methylene-tetrahydrofolate + L-Glutamate + Adenosine triphosphate > a 5,10-methylene-tetrahydrofolate + Phosphate + ADPRXN0-2921Putrescine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP + PhosphateRXN0-39014-(Glutamylamino) butanoate + Water > gamma-Aminobutyric acid + L-GlutamateRXN0-3942Water + p-Aminobenzoyl glutamate > p-Aminobenzoic acid + L-GlutamateRXN0-5040a [protein] α-L-glutamate + L-Glutamate + Adenosine triphosphate a [protein] α-L-glu-α-L-glu + ADP + PhosphateRXN0-6726L-Alanyl-L-Glutamate + Water > L-Alanine + L-GlutamateRXN0-6981glycyl-L-glutamate + Water > Glycine + L-GlutamateRXN0-6984N<SUP>2</SUP>-succinylglutamate + Water > Succinic acid + L-GlutamateSUCCGLUDESUCC-RXNOxoglutaric acid + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelateSUCCINYLDIAMINOPIMTRANS-RXNN2-Succinyl-L-ornithine + Oxoglutaric acid > N2-Succinyl-L-glutamic acid 5-semialdehyde + L-GlutamateSUCCORNTRANSAM-RXNL-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-GlutamateTYRAMINOTRANS-RXNL-Aspartic acid + Oxoglutaric acid > Oxalacetic acid + L-GlutamateL-Alanine + Oxoglutaric acid > Pyruvic acid + L-GlutamateAcetyl-CoA + L-Glutamate > CoA + N-acetyl-L-glutamateN-Acetylornithine + Oxoglutaric acid > N-Acetyl-L-glutamate 5-semialdehyde + L-GlutamateN-succinyl-L-2,6-diaminoheptanedioate + Oxoglutaric acid > N-Succinyl-2-amino-6-ketopimelate + L-GlutamateAdenosine triphosphate + L-Aspartic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-GlutamateN-Succinyl-L-glutamate + Water > Succinic acid + L-Glutamate2 Adenosine triphosphate + L-Glutamine + Carbonic acid + Water >2 ADP + Inorganic phosphate + L-Glutamate + CarbamoylphosphateL-Glutamate > gamma-Aminobutyric acid + Carbon dioxideL-Glutamate + Water + NADP > Oxoglutaric acid + Ammonia + NADPHGLUTDEHYD-RXNAdenosine triphosphate + tetrahydropteroyl-(gamma-Glu)(n) + L-Glutamate > ADP + Inorganic phosphate + tetrahydropteroyl-(gamma-Glu)(n+1)Adenosine triphosphate + 7,8-Dihydropteroic acid + L-Glutamate > ADP + Inorganic phosphate + Dihydrofolic acidgamma-Aminobutyric acid + Oxoglutaric acid > Succinic acid semialdehyde + L-GlutamateGABATRANSAM-RXN(S)-b-aminoisobutyric acid + Oxoglutaric acid > 2-Methyl-3-oxopropanoate + L-GlutamateL-Glutamine + Fructose 6-phosphate > L-Glutamate + D-glucosamine 6-phosphateAdenosine triphosphate + L-Glutamate + Ammonia > ADP + Inorganic phosphate + L-GlutamineL-Glutamine + Water > L-Glutamate + AmmoniaR00256GLUTAMIN-RXN2 L-Glutamate + NADP > L-Glutamine + Oxoglutaric acid + NADPHGLUTAMATESYN-RXNAdenosine triphosphate + L-Glutamate + L-Cysteine > ADP + Inorganic phosphate + gamma-GlutamylcysteineAdenosine triphosphate + Xanthylic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-Glutamine > imidazole-glycerol phosphate + N5-Carboxyaminoimidazole ribonucleotide + L-Glutamate + WaterHistidinol phosphate + Oxoglutaric acid > Imidazole acetol-phosphate + L-GlutamateHISTAMINOTRANS-RXNL-Leucine + Oxoglutaric acid > Ketoleucine + L-GlutamateL-Isoleucine + Oxoglutaric acid > (S)-3-methyl-2-oxopentanoate + L-GlutamateL-Valine + Oxoglutaric acid > a-Ketoisovaleric acid + L-GlutamateL-Glutamate > D-Glutamic acidChorismate + L-Glutamine > 4-Amino-4-deoxychorismate + L-GlutamatePutrescine + Oxoglutaric acid > L-Glutamate + 1-Pyrroline + Water5-Phosphoribosylamine + Pyrophosphate + L-Glutamate > L-Glutamine + Phosphoribosyl pyrophosphate + WaterAdenosine triphosphate + 5'-phosphoribosyl-N-formylglycinamide + L-Glutamine + Water > ADP + Inorganic phosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-Glutamate(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 Water > L-Glutamate + NAD(P)HAdenosine triphosphate + L-Glutamate + Putrescine > ADP + Inorganic phosphate + gamma-Glutamyl-L-putrescinePhosphoserine + Oxoglutaric acid > Phosphohydroxypyruvic acid + L-GlutamatePSERTRANSAM-RXNO-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-GlutamatePSERTRANSAMPYR-RXNAdenosine triphosphate + L-Glutamate + tRNA(Glu) > Adenosine monophosphate + Pyrophosphate + L-glutamyl-tRNA(Glu)Chorismate + L-Glutamine > 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateAn aromatic amino acid + Oxoglutaric acid > an aromatic oxo acid + L-GlutamateAdenosine triphosphate + Uridine triphosphate + L-Glutamine + Water + Ammonia <> ADP + Phosphate + Cytidine triphosphate + L-GlutamateR00573 2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + CarbamoylphosphateR00575 Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acidR04173 Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + WaterR10064 2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ionR00114 dTDP-D-Fucosamine + alpha-Ketoglutarate <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-GlutamateR04438 Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-GlutamateR03120 Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-GlutamateR00578 Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-GlutamateR01231 Adenosine triphosphate + THF-polyglutamate + L-Glutamate <> ADP + PhosphateR04241 Ammonia + L-Glutamic acid + Adenosine triphosphate + Oxoglutaric acid + L-Glutamate <> Phosphate + L-Glutamine + Adenosine diphosphate + ADPPW_R002433L-Glutamic acid + Adenosine triphosphate + Ammonium + L-Glutamate > L-Glutamine + Hydrogen ion + Adenosine diphosphate + Phosphate + ADPPW_R002665Hydrogen ion + NADPH + Ammonia + NADPH <> Water + NADP + L-Glutamic acid + L-GlutamatePW_R002434Oxoglutaric acid + NADPH + Ammonium + Hydrogen ion + NADPH > L-Glutamic acid + Water + NADP + L-GlutamatePW_R0026662 L-Glutamic acid + NADP + 2 L-Glutamate > L-Glutamine + NADPH + Hydrogen ion + Oxoglutaric acid + NADPHPW_R002435L-Glutamine + Oxoglutaric acid + NADPH + Hydrogen ion + NADPH >2 L-Glutamic acid + NADP +2 L-GlutamatePW_R002669L-Glutamine + Water > L-Glutamic acid + Ammonia + L-GlutamatePW_R002514L-Glutamic acid + L-Glutamate <> D-Glutamic acidPW_R002515N-Succinyl-2-amino-6-ketopimelate + L-Glutamic acid + L-Glutamate > N-Succinyl-L,L-2,6-diaminopimelate + Oxoglutaric acidPW_R002530L-Glutamic acid + Hydrogen ion + L-Glutamate > Carbon dioxide + 4-(Glutamylamino) butanoatePW_R005146L-Alanine + Oxoglutaric acid + L-Alanine <> L-Glutamic acid + Pyruvic acid + L-GlutamatePW_R002586Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + L-Asparagine + L-GlutamatePW_R002643L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid > Oxalacetic acid + L-Glutamic acid + L-GlutamatePW_R002644L-Glutamic acid + Oxalacetic acid + L-Glutamate > L-Aspartic acid + Oxoglutaric acid + L-Aspartic acidPW_R002667Pyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Alanine + L-AlaninePW_R002660a-Ketoisovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-ValinePW_R002663Isovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-ValinePW_R0028863-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-ValinePW_R003714L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acidPW_R002670N-acetyl-L-glutamate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-AcetylornithinePW_R002673N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-AcetylornithinePW_R002675Hydrogen carbonate + Water + L-Glutamine + 2 Adenosine triphosphate >2 Adenosine diphosphate + Phosphate + L-Glutamic acid +2 Hydrogen ion + Carbamoylphosphate +2 ADP + L-GlutamatePW_R002677N2-Succinyl-L-ornithine + Oxoglutaric acid > L-Glutamic acid + N2-Succinyl-L-glutamic acid 5-semialdehyde + L-GlutamatePW_R002680 N2-succinylglutamate + Water + N2-succinylglutamate > L-Glutamic acid + Succinic acid + L-GlutamatePW_R002682Putrescine + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Phosphate + Adenosine diphosphate + Hydrogen ion + gamma-Glutamyl-L-putrescine + ADPPW_R0026854-(Glutamylamino) butanoate + Water > L-Glutamic acid + gamma-Aminobutyric acid + L-GlutamatePW_R002688Putrescine + Oxoglutaric acid > L-Glutamic acid + 4-Aminobutyraldehyde + L-GlutamatePW_R002689Putrescine + Oxoglutaric acid <> L-Glutamic acid + 1-Pyrroline + Water + L-GlutamatePW_R005441gamma-Aminobutyric acid + Oxoglutaric acid > Succinic acid semialdehyde + L-Glutamic acid + L-GlutamatePW_R002691L-Glutamic acid + Adenosine triphosphate + L-Glutamate > Adenosine diphosphate + γ-L-glutamyl 5-phosphate + ADPPW_R002715L-Glutamic-gamma-semialdehyde + NAD + Water >2 Hydrogen ion + NADH + L-Glutamic acid + L-GlutamatePW_R002722L-Glutamic acid + Adenosine triphosphate + Hydrogen ion + tRNA(Glu) + L-Glutamate > Pyrophosphate + Adenosine monophosphate + L-glutamyl-tRNA(Glu)PW_R0028258 L-Glutamic acid + 8 Hydrogen ion + 8 Adenosine triphosphate + 8 tRNA(Glu) + 8 L-Glutamate >8 Adenosine monophosphate +8 Pyrophosphate +8 L-glutamyl-tRNA(Glu)PW_R003472Phosphohydroxypyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + DL-O-PhosphoserinePW_R0028442-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> A-Ketoglutaric acid oxime + O-Phospho-4-hydroxy-L-threoninePW_R0033244-hydroxyphenylpyruvate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Tyrosine + L-TyrosinePW_R002858Ketoleucine + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-LeucinePW_R002881Phenylpyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Phenylalanine + L-PhenylalaninePW_R002861L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threoninePW_R003321L-Glutamic acid + L-Glutamate <> Oxoglutaric acid + O-Phospho-4-hydroxy-L-threoninePW_R003322L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + A-Ketoglutaric acid oximePW_R0033232-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acidPW_R003326Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-GlutamatePW_R002869Imidazole acetol-phosphate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-histidinol-phosphatePW_R0028713-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Isoleucine + L-IsoleucinePW_R002928L-Aspartic acid + Water + Adenosine triphosphate + L-Glutamine + L-Aspartic acid > L-Asparagine + Hydrogen ion + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate + L-Asparagine + L-GlutamatePW_R002887Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-GlutamatePW_R002894Nicotinic acid adenine dinucleotide + Water + L-Glutamine + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + NAD + L-GlutamatePW_R003011L-Glutamic acid + Adenosine triphosphate + L-Cysteine + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + gamma-Glutamylcysteine + ADPPW_R003052D-tagatofuranose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamic acid + L-GlutamatePW_R003307Fructose 6-phosphate + L-Glutamine + Fructose 6-phosphate > L-Glutamic acid + Glucosamine 6-phosphate + L-GlutamatePW_R003565UDP-β-L-threo-pentapyranos-4-ulose + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinosePW_R003357Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismatePW_R0034037,8-Dihydropteroic acid + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + 7,8-dihydrofolate monoglutamate + ADP + Dihydrofolic acidPW_R003404Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-GlutamatePW_R0034105'-Phosphoribosyl-N-formylglycinamide + Water + L-Glutamine + Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide > 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + Phosphate + Adenosine diphosphate + Hydrogen ion + L-Glutamate + ADPPW_R003413Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-GlutamatePW_R003427Uridine triphosphate + L-Glutamine + Water + Adenosine triphosphate + Uridine triphosphate > Adenosine diphosphate + Hydrogen ion + Phosphate + L-Glutamic acid + Cytidine triphosphate + ADP + L-GlutamatePW_R003533L-Glutamic acid + dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-thomosaminePW_R003704Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acidPW_R005149L-Glutamic acid + Adenosine triphosphate + Water + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Glutamic acid + ADPPW_RCT000102Cysteic acid + Oxoglutaric acid <> L-Glutamate + 3-Sulfopyruvic acidPW_R005927L-Glutamate + 3-Cyano-L-alanine > Water + gamma-Glutamyl-beta-cyanoalaninePW_R005915gamma-glutamyl-gamma-aminobutyrate + Water > gamma-Aminobutyric acid + L-GlutamatePW_R006001dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-D-FucosaminePW_R005969D-tagatofuranose 6-phosphate + L-Glutamine <> D-glucosamine 6-phosphate + L-GlutamatePW_R006103gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehydebeta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-GlutamateChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-GlutamateL-D-1-Pyrroline-5-carboxylic acid + 2 Water + NAD > L-Glutamate + Hydrogen ion + NADHN-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamatealpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelateGlutathione + Water > Cysteinylglycine + L-GlutamateL-Glutamine + Water <> L-Glutamate + Ammoniaalpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidL-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine5 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + WaterAdenosine triphosphate + 7 7,8-Dihydropteroic acid + L-Glutamate <> ADP + Dihydrofolic acid + Hydrogen ion + PhosphatetRNA(Glu) + L-Glutamate + Adenosine triphosphate <> L-Glutamyl-tRNA(Glu) + Pyrophosphate + Adenosine monophosphatealpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acidL-Glutamate + 2 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonineL-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinoseAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + PyrophosphateAdenosine triphosphate + L-Glutamate <> ADP + L-Glutamic acid 5-phosphateL-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ionD-Glutamic acid <> L-Glutamate2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphatealpha-Ketoglutarate + L-Isoleucine <>3 3-Methyl-2-oxovaleric acid + L-Glutamatealpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPAdenosine triphosphate + L-Glutamate + Ammonia <> ADP + Phosphate + L-GlutamineAdenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + PhosphateAcetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acidFructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamategamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehydeChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidL-D-1-Pyrroline-5-carboxylic acid + 2 Water + NAD > L-Glutamate + Hydrogen ion + NADHGlutathione + Water > Cysteinylglycine + L-GlutamateL-Glutamine + Water <> L-Glutamate + AmmoniaChorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamatealpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidL-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylaminealpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acidPhosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + PhosphoserineAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + PyrophosphateAdenosine triphosphate + L-Glutamate <> ADP + L-Glutamic acid 5-phosphateD-Glutamic acid <> L-Glutamatealpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphatealpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ionalpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPAdenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + PhosphateFructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-GlutamateGutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture96000.0uM0.037 oCK12 NCM3722Mid-Log Phase3840000000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolShake flask and filter culture149000.0uM0.037 oCK12 NCM3722Mid-Log Phase5960000000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateShake flask and filter culture44800.0uM0.037 oCK12 NCM3722Mid-Log Phase1792000000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.1956162148 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h4270.0uM0.037 oCBW25113Stationary Phase, glucose limited170800000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776Luria-Bertani (LB) mediaShake flask259.0uMtrue45.037 oCBL21 DE3Stationary phase cultures (overnight culture)1037600180000Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911