2.02012-05-31 10:24:41 -06002015-09-13 15:15:18 -0600ECMDB00243M2MDB000102Pyruvic acidPyruvic acid is an alpha-keto acid. It can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA. It can also be used to construct the amino acid alanine and be converted into ethanol. Pyruvic acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactic acid when oxygen is lacking (fermentation).α-ketopropionateα-ketopropionic acid2-Oxo-propionate2-Oxo-propionic acid2-Oxopropanoate2-Oxopropanoic acid2-Oxopropionate2-Oxopropionic acidA-KetopropionateA-Ketopropionic acidAcetylformateAcetylformic acidAlpha-KetopropionateAlpha-Ketopropionic acidBTSPyroracematePyroracemic acidPyruvatePyruvic acidα-Ketopropionateα-Ketopropionic acidC3H4O388.062188.0160439942-oxopropanoic acidpyruvic acid127-17-3CC(=O)C(O)=OInChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)LCTONWCANYUPML-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmlogp-0.38logs0.18solubility1.34e+02 g/lmelting_point13.8 oClogp0.066pka_strongest_acidic2.93pka_strongest_basic-9.6iupac2-oxopropanoic acidaverage_mass88.0621mono_mass88.016043994smilesCC(=O)C(O)=OformulaC3H4O3inchiInChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)inchikeyLCTONWCANYUPML-UHFFFAOYSA-Npolar_surface_area54.37refractivity17.99polarizability7.31rotatable_bond_count1acceptor_count3donor_count1physiological_charge-1formal_charge0Pentose phosphate pathwayec00030Citrate cycle (TCA cycle)ec00020Butanoate metabolismec00650Reductive carboxylate cycle (CO2 fixation)ec00720Alanine, 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 metabolismec00230Cysteine 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 biosynthesisec00400Carbon fixation in photosynthetic organismsec00710Glycine, serine and threonine metabolismec00260Glycolysis / Gluconeogenesisec00010Fructose and mannose metabolismec00051Galactose metabolismGalactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase.
Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell
PW000821ec00052MetabolicAscorbate and aldarate metabolismec00053Amino 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.
PW000908ec00790MetabolicPyruvate metabolismec00620Methane 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 metabolismec00750Selenoamino acid metabolismec00450Sulfur metabolismThe sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion.
The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described.
The third variant of sulfur metabolism starts with the import of an alkyl sulfate into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. The alkyl sulfate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000922ec00920MetabolicPentose and glucuronate interconversionsec00040Tryptophan 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
PW000815ec00380MetabolicGlyoxylate and dicarboxylate metabolismec00630Nicotinate and nicotinamide metabolismec00760D-Alanine metabolismL-alanine is an essential component of protein 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.
Refer to L-alanine metabolism (pathway PW000788 ).
Through this single pathway D-alanine can be degraded to pyruvate through a D-amino acid dehydrogenase, which enters 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. 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.
PW000768ec00473MetabolicPropanoate 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 metabolismec00430Thiamine metabolismec00730Ubiquinone and other terpenoid-quinone biosynthesisec00130Trinitrotoluene degradationec00633Biosynthesis of siderophore group nonribosomal peptides2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate.
The biosynthesis of 2,3-dihydroxybenzoate starts from chorismate being synthesized into isochorismate through isochorismate synthase entC. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.This compound then interacts with L-serine and ATP through enterobactin synthase protein complex resulting in the production of enterobactin. Enterobactin is exported into the periplasmic space through the enterobactin exporter entS. The compound is the export to the environment through the outer membrane protein TolC. In the environment enterobactin reacts with iron to produce Ferric enterobactin. This compound is imported into the periplasmic space through a ferric enterobactin outermembrane transport complex. The compound then enters the cytoplasm through a ferric enterobactin ABC transporter.Once inside the cytoplasm, ferric enterobactin spontaneously releases the iron ion from the enterobactin.
PW000760ec01053MetabolicBenzoate degradation via hydroxylationec00362Terpenoid backbone biosynthesisec00900Biphenyl degradationec00621Toluene and xylene degradationec00622Microbial metabolism in diverse environmentsec01120Phosphotransferase system (PTS)ec02060Monobactam biosynthesiseco00261Metabolic pathwayseco011002,3-dihydroxybenzoate biosynthesis2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds.
The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes EntC, EntB, and EntA. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.
PW000751Metabolic2-Oxopent-4-enoate metabolismThe pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate.
The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate.
The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW001890MetabolicGalactitol and galactonate degradationD-galactonate can serve as the sole source of carbon and energy for E. coli . The initial step, after the transport of galactonic acid into the cell is the degradation of D-galactonate is dehydration to 2-dehydro-3-deoxy-D-galactonate by D-galactonate dehydratase. Subsequent phosphorylation by 2-dehydro-3-deoxygalactonate kinase and aldol cleavage by 2-oxo-3-deoxygalactonate 6-phosphate aldolase produce pyruvate and D-glyceraldehyde-3-phosphate, which enter central metabolism.
Galactitol can also be utilized by E. coli K-12 as a total source of carbon and energy. Each enters the cell via a specific phosphotransferase system, so the first intracellular species is D-galactitol-1-phosphate or D-galactitol-6-phosphate, which are identical. This sugar alcohol phosphate becomes the substrate for a dehydrogenase that oxidizes its 2-alcohol group to a keto group. Galactitol-1-phosphate, the product of the dehydrogenation is tagatose-6-phosphate, which becomes the substrate of a kinase and subsequently an aldolase (in a pair of reactions that parallel those of glycolysis) before it is converted into intermediates (D-glyceraldehde-3-phosphate and dihydroxy-acetone-phosphate) of glycolysis.PW000820MetabolicGluconeogenesis from L-malic acidGluconeogenesis from L-malic acid starts from the introduction of L-malic acid into cytoplasm either through a C4 dicarboxylate / orotate:H+ symporter or a dicarboxylate transporter (succinic acid antiporter). L-malic acid is then metabolized through 3 possible ways: NAD driven malate dehydrogenase resulting in oxalacetic acid, NADP driven malate dehydrogenase B resulting pyruvic acid or malate dehydrogenase, NAD-requiring resulting in pyruvic acid.
Oxalacetic acid is processed by phosphoenolpyruvate carboxykinase (ATP driven) while pyruvic acid is processed by phosphoenolpyruvate synthetase resulting in phosphoenolpyruvic acid. This compound is dehydrated by enolase resulting in an 2-phosphoglyceric acid. This compound is then isomerized by 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 3-phosphoglyceric acid which is phosphorylated by an ATP driven phosphoglycerate kinase resulting in an glyceric acid 1,3-biphosphate. This compound undergoes an NADH driven glyceraldehyde 3-phosphate dehydrogenase reaction resulting in a D-Glyceraldehyde 3-phosphate which is first isomerized into dihydroxyacetone phosphate through an triosephosphate isomerase. D-glyceraldehyde 3-phosphate and Dihydroxyacetone phosphate react through a fructose biphosphate aldolase protein complex resulting in a fructose 1,6-biphosphate. This compound is metabolized by a fructose-1,6-bisphosphatase resulting in a Beta-D-fructofuranose 6-phosphate which is then isomerized into a Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.
PW000819MetabolicL-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.
PW000788MetabolicMenaquinol biosythesisMenaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate.
The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol.PW001897MetabolicS-adenosyl-L-methionine biosynthesisS-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environmentPW000837MetabolicSecondary Metabolites: Ubiquinol biosynthesisThe biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate.
The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol.
The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol.
The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8.
PW000981MetabolicSecondary 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: threonine biosynthesis from aspartateThe biosynthesis of threonine starts with L-aspartic acid being 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. PW000976MetabolicValine 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 1430936196PW000891Metabolicfructose metabolismFructose metabolism begins with the transport of Beta-D-fructofuranose through a fructose PTS permease, resulting in a Beta-D-fructofuranose 1-phosphate. This compound is phosphorylated by an ATP driven 1-phosphofructokinase resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid.
Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.
PW000913Metabolicfucose and rhamnose degradationIn E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Via reactions catalyzed by proteins encoded in linked operons comprising a regulon, the methylpentose, alpha-L-rhamnopyranose and/or beta-L-rhamnopyranose, is taken into the cell through a proton symporter and metabolized, enabling E. coli to grow on it as a total source of carbon and energy.
For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde.
For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde.
Two pathways can be used for degradation of L-lactaldehyde. Aerobically, it is converted via lactate to pyruvate, also an intermediate of glycolysis. Anaerobically, lactaldehyde reductase is induced which converts lactaldehyde into propane-1,2-diol. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment.
PW000826Metabolicglycerol metabolismGlycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through a glycerophosphodiester reacting with water through a glycerophosphoryl diester phosphodiesterase or it can also be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter.
Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+].
Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000914Metabolicglycerol metabolism IIGlycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphocholine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000915Metabolicglycerol metabolism III (sn-glycero-3-phosphoethanolamine)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphethanolamine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000916Metabolicglycerol metabolism IV (glycerophosphoglycerol)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoglycerol reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000917Metabolicglycerol metabolism V (glycerophosphoserine)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoserine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000918Metabolicglycolysis and pyruvate dehydrogenaseFructose metabolism begins with the transport of Beta-D-glucose 6-phosphate through a glucose PTS permease, resulting in a Beta-D-glucose 6-phosphate. This compound is isomerized by a glucose-6-phosphate isomerase resulting in a fructose 6-phosphate. This compound can be phosphorylated by two different enzymes, a pyridoxal phosphatase/fructose 1,6-bisphosphatase or a ATP driven-6-phosphofructokinase-1 resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid.
Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.
PW000785Metabolichexuronide and hexuronate degradationE. coli can use β-D-glucuronosides, D-glucuronate and D-fructuronate as an only sources of carbon for growth.
β-D-glucuronosides are detoxification products that are excreted into the mammalian gut in the bile. They enter E.coli through an outer membrane protein called gusC. Once in the periplasmic space it is transported through a hydrogen symporter into the cytoplasm.
Once inside the cytoplasm, the initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate. This is then isomerized to D-fructuronate by D-glucuronate isomerase. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate.This product is then process by KHG/KDPG aldolase which in turn produces D-Glyceraldehyde 3-phosphate and Pyruvic Acid which then go into their respective sub pathways: glycolysis and pyruvate dehydrogenase
The pathway can also start from 3 other points: a hydrogen ion symporter (gluconate/fructuronate transporter GntP) of D-fructuronate, a hydrogen ion symporter (Hexuronate transporter) of aldehydo-D-galacturonate that spontaneously turns into D-tagaturonate and then undergoes an NADH-dependent reduction to D-altronate through an altronate oxidoreductase. D-altronate undergoes dehydration to yield 2-dehydro-3-deoxy-D-gluconate, the third and last point where the reaction can start from a hydrogen symporter of a 2-dehydro-3-deoy-D-gluconate.PW000834Metabolicisoleucine 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.
PW000818Metabolicserine 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.
PW000809Metabolicsulfur metabolism (butanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case 1-butanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. 1-butanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000923Metabolicsulfur metabolism (ethanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case ethanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Ethanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000925Metabolicsulfur metabolism (isethionate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case isethionate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Isethionate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000926Metabolicsulfur metabolism (methanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case methanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Methanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000927Metabolicsulfur metabolism (propanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case 3-(N-morpholino)propanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. 3-(N-morpholino)propanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000924Metabolicsuperpathway of D-glucarate and D-galactarate degradation
Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth.
The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--).
The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde.
Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA.
The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid.
The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid.PW000795Metabolictryptophan 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-CoAPW001916Metabolicketogluconate metabolismPW002003Metabolic2-Oxopent-4-enoate metabolism 2The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW002035MetabolicEnterobactin BiosynthesisEnterobactin is a catecholate siderophore produced almost exclusively by enterobacteria, although it has been reported in some Streptomyces species. It is a cyclic compound made of three units of 2,3-dihydroxybenzoylserine joined in a cyclic structure by lactone linkages (only the δ-cis isomer of the ferric chelate is biologically active). Not only the cyclic molecule, but also the biosynthetic precursor 2,3-dihydroxy-N-benzoylserine and its linear dimer and trimer condensation products are able to transport iron into enterobacteria.
Enterobactin is synthesized under iron-deficient conditions and excreted into the environment where it binds Fe(III) with high affinity and specificity. The ferrisiderophore complexes are taken up into the cell by specific transport components. Enterobactin synthesis is divided into two parts: 1) the conversion of chorismate to 2,3-dihydroxybenzoate 2) the synthesis of enterobactin from 2,3-dihydroxybenzoate and L-serine. (EcoCyc)PW002048MetabolicHydrogen 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.PW002066MetabolicL-lactaldehyde degradation (aerobic)L-lactaldehyde is one of two products resulting from degradation of the two methylpentoses L-fucose and rhamnose, which are metabolized by an analogous series of reactions.
Aerobically, lactaldehyde is oxidized in two steps to pyruvate, which enters central metabolism.PW002073MetabolicN-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradationThe degradation of N-acetylneuraminate begins with its incorporation into the cytosol through a hydrogen symporter. Once inside the cytosol it is degraded by a N-acetylneuraminate lyase resulting in a release of a pyruvic acid and N-acetymannosamine. The latter compound is phosphorylated by an ATP driven N-Acetylmannosamine kinase resulting in the release of an ADP, a hydrogen ion and a N-Acetyl-D-mannosamine 6-phosphate. This phosphorylated compound is then metabolized by a putative N-acetylmannosamine-6-phosphate 2-epimerase resulting in the release of a N-Acetyl-D-glucosamine 6-phosphate. This compound is then deacetylated through a N-acetylglucosamine-6-phosphate deacetylase resulting in the release of an Acetic acid and a glucosamine 6-phosphate This compound can then be deaminated through a glucosamine-6-phosphate deaminase resulting in the release of an ammonium and a beta-D-fructofuranose 6-phosphate which can then be incorporated into the glycolysis pathway.
PW002030MetabolicSecondary Metabolites: Ubiquinol biosynthesis 2The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8.PW002036MetabolicSpermidine Biosynthesis ISpermidine is formed by the addition of a propylamine moiety to putrescine, catalyzed by an aminopropyltransferase termed spermidine synthase, the the product of gene speE. The source of the propylamine group is decarboxylated S-adenosyl-L-methionine (S-adenosyl-L-methioninamine) which is produced by the action of the pyruvoyl-containing enzyme adenosylmethionine decarboxylase. The other product of the aminopropyltransferase reaction is S-methyl-5'-thioadenosine (MTA), which can be recycled back to L-methionine in many organisms, but not in E. coli.
Inhibition of E. coli adenosylmethionine decarboxylase by spermidine appears to be the most significant regulator of polyamine biosynthesis, probably limiting it when the intracellular spermidine concentration becomes excessive. In E. coli most intracellular spermidine is bound to nucleic acids and phospholipids. (EcoCyc)PW002040MetabolicThiazole Biosynthesis IThis pathway describes only the synthesis of the thiazole moiety of thiamin. Different variations of this pathway exist, this particular pathway describes the pathway that occurs in Escherichia coli K-12 and Salmonella enterica enterica serovar Typhimurium.
The biosynthesis of the thiazole moiety is complex. In Escherichia coli it involves six proteins, the products of the thiS, thiF, thiG, thiH, thiI, and iscS genes.
The process begins when IscS, a protein that is also involved in the biosynthesis of iron-sulfur clusters, catalyzes the transfer of a sulfur atom from cysteine to a ThiI sulfur-carrier protein, generating a an S-sulfanyl-[ThiI sulfur-carrier protein].
In a parallel route, the ThiF protein activates a ThiS sulfur-carrier protein by adenylation of its carboxy terminus, generating a carboxy-adenylated-[ThiS sulfur-carrier protein]. In a second reaction, which may also be catalyzed by ThiF, the sulfur from an S-sulfanyl-[ThiI sulfur-carrier protein] is transferred to ThiS, generating a thiocarboxy-[ThiS-Protein].
The final reaction of this pathway, which is catalyzed by the ThiG protein, requires three inputs: a thiocarboxy-[ThiS-Protein], 1-deoxy-D-xylulose 5-phosphate and 2-iminoacetate.
2-iminoacetate is formed in Escherichia coli from L-tyrosine by tyrosine lyase (ThiH), which forms a complex with ThiG.
For many years the products of this reaction was assumed to be 4-methyl-5-(β-hydroxyethyl)thiazole (thiazole). However, recent work performed with the thiazole synthase from Bacillus subtilis has shown that the actual product is the thiazole tautomer 2-[(2R,5Z)-(2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate. While in Bacillus a dedicated thiazole tautomerase converts this product into a different tautomer (2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate), most of the proteobacteria lack the tautomerase. (EcoCyc)PW002041MetabolicD-serine degradationThe degradation of D-serine begins with the transport of D-serine into the cytosol through a cycA. Once in the cytosol D-serine reacts with ammonia-lyase resulting in the release of a hydrogen ion, water and a 2-aminoprop-2-enoate. This compound in turn reacts spontaneously to produces 2-iminipropanoate. This compound in turn reacts with water and hydrogen ion spontaneously resulting in the release of ammonium and apyruvate.PW002101MetabolicL-cysteine degradationThe degradation of cysteine starts with L-cysteine reacting with l-cysteine desulfhydrase resulting in the release of a hydrogen sulfide, a hydrogen ion and a a 2-aminoprop-2-enoate. The latter compound in turn reacts spontaneously to form a 2-iminopropanoate. This compound in turn reacts spontaneously with water and a hydrogen ion resulting in the release of ammonium and pyruvate.PW002110MetabolicSpermidine biosynthesis and metabolismSpermidine metabolism starts with S-adenosyl-L-methionine reacting with a hydrogen ion through a adenosylmethionine decarboxylase resulting in the release of a carbon dioxide and a S-adenosyl 3-(methylthio)propylamine. The later compound in turn reacts with putrescine resulting in the release of a hydrogen ion, a spermidine and a S-methyl-5'-thioadenosine. S-methyl-5'-thioadenosine in turn reacts with a water molecule through a 5-methylthioadenosine nucleosidase resulting in the release of a adenine and a S-methyl-5-thio-D-ribose which in in turn is released into the environment. PW002085Metabolicmethylglyoxal degradation IIThe most common pathway for methylglyoxal detoxification is the glyoxalase system, which is composed of two enzymes that together convert methylglyoxal to (R)-lactate in the presence of glutathione. However, in E. coli, a single enzyme, glyoxalase III, catalyzes this conversion in a single step without involvement of glutathione. Activity of glyoxalase III increases at the transition to stationary phase and expression is dependent on RpoS, suggesting that this pathway may be important during stationary phase. (EcoCyc)PW002084Metabolicmethylglyoxal degradation IVIn this pathway, which has been characterized in Escherichia coli K-12, methylglyoxal is reduced to lactaldehyde by the enzyme methylglyoxal reductase. (S)-lactaldehyde is then reduced to (S)-lactate which is finally converted to pyruvate and joins the pool of central metobolites.
Methylglyoxal reductases have been characterized in bacteria and fungi. Some of the enzymes are NADP-linked, while others are NAD-linked. Two variants of this pathway have been entered in MetaCyc to reflect the different biochemistry of the last enzyme, L-lactate dehydrogenase. The Escherichia coli K-12 enzyme encoded by gene lldD uses an unidentified electron acceptor, while the Saccharomyces cerevisiae enzyme uses an an oxidized c-type cytochrome. (EcoCyc)PW002078Metabolicpyruvate decarboxylation to acetyl CoAThis multi-enzyme complex, which consists of 24 subunits of pyruvate dehydrogenase, 24 subunits of lipoate acetyltransferase, and 12 subunits of dihydrolipoate dehydrogenase, catalyzes three reactions, which constitute a cycle. The complex contains a lipoyl active site in the form of lipoyllysine, as well as a thiamin diphosphate.
The net consequence of the cycle, in addition to reducing NAD+, is the conversion of pyruvate into acetyl-CoA and CO2, a key reaction of central metabolism because it links glycolysis I, which generates pyruvate, to the TCA cycle, into which the acetyl-CoA flows.
During aerobic growth the cycle is an essential source of acetyl-CoA to feed the TCA cycle and thereby to satisfy the cellular requirements for the precursor metabolites it forms. Mutant strains defective in the complex require an exogenous source of acetate to meet this requirement, but anaerobically such mutants grow without exogenous acetate because under such conditions, pyruvate formate lyase generates acetyl-CoA from pyruvate. Mutant strains lacking pyruvate formate lyase have the reverse phenotype. They require acetate for anaerobic but not for aerobic growth.PW002083Metabolicpyruvate to cytochrome bd terminal oxidase electron transferThe reaction of pyruvate to cytochrome bd terminal oxidase electron transfer starts with 2 pyruvate and 2 water molecules reacting in a pyruvate oxidase resulting in the release of 4 electrons into the inner membrane, and releasing 2 carbon dioxide molecules , 2 acetate and 4 hydrogen ion into the cytosol.
2 ubiquinone,4 hydrogen ion and 4 electron ion react resulting in the release of 2 ubiquinol . The 2 ubiquinol in turn release 4 hydrogen ions into the periplasmic space through a cytochrome bd-I terminal oxidase and releasing 4 electrons through the enzyme. Oxygen and 4 hydrogen ion reacts with the 4 electrons resulting in 2 water molecules.PW002087Metabolicisoleucine biosynthesis I (from threonine)ILEUSYN-PWYpyruvate oxidation pathwayPYRUVOX-PWYmixed acid fermentationFERMENTATION-PWYthiazole biosynthesis I (E. coli)PWY-6892gluconeogenesis IGLUCONEO-PWYglycolysis IGLYCOLYSIS1,4-dihydroxy-2-naphthoate biosynthesis IPWY-58372-methylcitrate cycle IPWY0-42tryptophan degradation II (via pyruvate)TRYPDEG-PWYL-serine degradationSERDEG-PWYD-serine degradationPWY0-1535methionine biosynthesis IHOMOSER-METSYN-PWYL-cysteine degradation IILCYSDEG-PWYrespiration (anaerobic)ANARESP1-PWYmethylerythritol phosphate pathwayNONMEVIPP-PWYmethylglyoxal degradation IPWY-5386glycerol degradation VGLYCEROLMETAB-PWYalanine biosynthesis IIALANINE-SYN2-PWYalanine biosynthesis IALANINE-VALINESYN-PWYvaline biosynthesisVALSYN-PWYhydrogen sulfide biosynthesisPWY0-1534<i>p</i>-aminobenzoate biosynthesisPWY-6543pyridoxal 5'-phosphate biosynthesis IPYRIDOXSYN-PWYlysine biosynthesis IDAPLYSINESYN-PWYtryptophan biosynthesisTRPSYN-PWYalanine degradation IALADEG-PWYL-lactaldehyde degradation (aerobic)PWY0-1317acetyl-CoA biosynthesis I (pyruvate dehydrogenase complex)PYRUVDEHYD-PWYsuperpathway of glycolysis, pyruvate dehydrogenase, TCA, and glyoxylate bypassGLYCOLYSIS-TCA-GLYOX-BYPASSmethylglyoxal degradation IIPWY-901D-malate degradationPWY0-14652,3-dihydroxybenzoate biosynthesisPWY-5901D-galactonate degradationGALACTCAT-PWYD-galactarate degradation IGALACTARDEG-PWY<i>D</i>-glucarate degradation IGLUCARDEG-PWYEntner-Doudoroff pathway IENTNER-DOUDOROFF-PWY<i>N</i>-acetylneuraminate and <i>N</i>-acetylmannosamine degradationPWY0-13244-hydroxybenzoate biosynthesis II (bacteria and fungi)PWY-57552-oxopentenoate degradationPWY-5162Specdb::CMs856Specdb::CMs904Specdb::CMs911Specdb::CMs3173Specdb::CMs29477Specdb::CMs30679Specdb::CMs31099Specdb::CMs31100Specdb::CMs32376Specdb::CMs37382Specdb::CMs136757Specdb::CMs144491Specdb::CMs1055177Specdb::CMs1055178Specdb::CMs1055180Specdb::EiMs508Specdb::NmrOneD1215Specdb::NmrOneD1266Specdb::NmrOneD2212Specdb::NmrOneD2905Specdb::NmrOneD4784Specdb::NmrOneD4785Specdb::NmrOneD4786Specdb::NmrOneD4787Specdb::NmrOneD143150Specdb::NmrOneD143151Specdb::NmrOneD143152Specdb::NmrOneD143153Specdb::NmrOneD143154Specdb::NmrOneD143155Specdb::NmrOneD143156Specdb::NmrOneD143157Specdb::NmrOneD143158Specdb::NmrOneD143159Specdb::NmrOneD143160Specdb::NmrOneD143161Specdb::NmrOneD143162Specdb::NmrOneD143163Specdb::NmrOneD143164Specdb::NmrOneD143165Specdb::NmrOneD143166Specdb::MsMs6147Specdb::MsMs6148Specdb::MsMs6149Specdb::MsMs6150Specdb::MsMs6151Specdb::MsMs6152Specdb::MsMs179619Specdb::MsMs179620Specdb::MsMs179621Specdb::MsMs181950Specdb::MsMs181951Specdb::MsMs181952Specdb::MsMs438249Specdb::MsMs438250Specdb::MsMs438251Specdb::MsMs438252Specdb::MsMs438253Specdb::MsMs2237218Specdb::MsMs2240238Specdb::MsMs2241457Specdb::MsMs2242358Specdb::MsMs2243524Specdb::MsMs2456955Specdb::MsMs2456956Specdb::MsMs2456957Specdb::NmrTwoD1233HMDB002431031C0002215361PYRUVATEPYRPyruvic 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). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92.6581765Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.12097436Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25.15627241Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18.15882454Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36.8579834Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.8412012Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.8087979Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72.688619Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2.7819686Ka T, Yamamoto T, Moriwaki Y, Kaya M, Tsujita J, Takahashi S, Tsutsumi Z, Fukuchi M, Hada T: Effect of exercise and beer on the plasma concentration and urinary excretion of purine bases. J Rheumatol. 2003 May;30(5):1036-42.12734903Talseth T, Haegele KD, McNay JL, Skrdlant HB, Clementi WA, Shepherd AM: Pharmacokinetics and cardiovascular effects in rabbits of a major hydralazine metabolite, the hydralazine pyruvic-acid hydrazone. J Pharmacol Exp Ther. 1979 Dec;211(3):509-13.512915Reece PA, Cozamanis I, Zacest R: Selective high-performance liquid chromatographic assays for hydralazine and its metabolites in plasma of man. J Chromatogr. 1980 Mar 14;181(3-4):427-40.7391156Meijer-Severs GJ, Van Santen E, Meijer BC: Short-chain fatty acid and organic acid concentrations in feces of healthy human volunteers and their correlations with anaerobe cultural counts during systemic ceftriaxone administration. Scand J Gastroenterol. 1990 Jul;25(7):698-704.2396083Elling D, Bader K: [Biochemical changes in cervix mucus in stepwise malignant transformation of cervix epithelium] Zentralbl Gynakol. 1990;112(9):555-60.2378186Mongan PD, Capacchione J, West S, Karaian J, Dubois D, Keneally R, Sharma P: Pyruvate improves redox status and decreases indicators of hepatic apoptosis during hemorrhagic shock in swine. Am J Physiol Heart Circ Physiol. 2002 Oct;283(4):H1634-44. Epub 2002 Jun 20.12234818Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.http://hmdb.ca/system/metabolites/msds/000/000/177/original/HMDB00243.pdf?1358895516PTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlAcetolactate synthase isozyme 3 large subunitP00893ILVI_ECOLIilvIhttp://ecmdb.ca/proteins/P00893.xmlAcetolactate synthase isozyme 3 small subunitP00894ILVH_ECOLIilvHhttp://ecmdb.ca/proteins/P00894.xmlAnthranilate synthase component 1P00895TRPE_ECOLItrpEhttp://ecmdb.ca/proteins/P00895.xmlAnthranilate synthase component IIP00904TRPG_ECOLItrpDhttp://ecmdb.ca/proteins/P00904.xmlD-serine dehydrataseP00926SDHD_ECOLIdsdAhttp://ecmdb.ca/proteins/P00926.xmlThreonine dehydratase biosyntheticP04968THD1_ECOLIilvAhttp://ecmdb.ca/proteins/P04968.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIA componentP05706PTHA_ECOLIsrlBhttp://ecmdb.ca/proteins/P05706.xmlD-lactate dehydrogenaseP06149DLD_ECOLIdldhttp://ecmdb.ca/proteins/P06149.xmlCystathionine beta-lyase metCP06721METC_ECOLImetChttp://ecmdb.ca/proteins/P06721.xmlDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complexP06959ODP2_ECOLIaceFhttp://ecmdb.ca/proteins/P06959.xmlPyruvate dehydrogenase [cytochrome]P07003POXB_ECOLIpoxBhttp://ecmdb.ca/proteins/P07003.xmlAcetolactate synthase isozyme 1 large subunitP08142ILVB_ECOLIilvBhttp://ecmdb.ca/proteins/P08142.xmlPTS system beta-glucoside-specific EIIBCA componentP08722PTV3B_ECOLIbglFhttp://ecmdb.ca/proteins/P08722.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlValine--pyruvate aminotransferaseP09053AVTA_ECOLIavtAhttp://ecmdb.ca/proteins/P09053.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlFormate acetyltransferase 1P09373PFLB_ECOLIpflBhttp://ecmdb.ca/proteins/P09373.xmlD-amino acid dehydrogenase small subunitP0A6J5DADA_ECOLIdadAhttp://ecmdb.ca/proteins/P0A6J5.xmlDihydrodipicolinate synthaseP0A6L2DAPA_ECOLIdapAhttp://ecmdb.ca/proteins/P0A6L2.xmlN-acetylneuraminate lyaseP0A6L4NANA_ECOLInanAhttp://ecmdb.ca/proteins/P0A6L4.xmlSerine hydroxymethyltransferaseP0A825GLYA_ECOLIglyAhttp://ecmdb.ca/proteins/P0A825.xmlTryptophanaseP0A853TNAA_ECOLItnaAhttp://ecmdb.ca/proteins/P0A853.xmlKHG/KDPG aldolaseP0A955ALKH_ECOLIedahttp://ecmdb.ca/proteins/P0A955.xmlPyruvate formate-lyase 1-activating enzymeP0A9N4PFLA_ECOLIpflAhttp://ecmdb.ca/proteins/P0A9N4.xmlDihydrolipoyl dehydrogenaseP0A9P0DLDH_ECOLIlpdAhttp://ecmdb.ca/proteins/P0A9P0.xml2-hydroxy-3-oxopropionate reductaseP0ABQ2GARR_ECOLIgarRhttp://ecmdb.ca/proteins/P0ABQ2.xmlPyruvate kinase IP0AD61KPYK1_ECOLIpykFhttp://ecmdb.ca/proteins/P0AD61.xmlAcetolactate synthase isozyme 1 small subunitP0ADF8ILVN_ECOLIilvNhttp://ecmdb.ca/proteins/P0ADF8.xmlAcetolactate synthase isozyme 2 small subunitP0ADG1ILVM_ECOLIilvMhttp://ecmdb.ca/proteins/P0ADG1.xmlIsochorismataseP0ADI4ENTB_ECOLIentBhttp://ecmdb.ca/proteins/P0ADI4.xmlPyruvate dehydrogenase E1 componentP0AFG8ODP1_ECOLIaceEhttp://ecmdb.ca/proteins/P0AFG8.xmlThreonine dehydratase catabolicP0AGF6THD2_ECOLItdcBhttp://ecmdb.ca/proteins/P0AGF6.xmlL-serine dehydratase 1P16095SDHL_ECOLIsdaAhttp://ecmdb.ca/proteins/P16095.xmlPTS system maltose- and glucose-specific EIICB componentP19642PTOCB_ECOLImalXhttp://ecmdb.ca/proteins/P19642.xmlPTS system fructose-specific EIIBC componentP20966PTFBC_ECOLIfruAhttp://ecmdb.ca/proteins/P20966.xmlPyruvate kinase IIP21599KPYK2_ECOLIpykAhttp://ecmdb.ca/proteins/P21599.xmlProtein malYP23256MALY_ECOLImalYhttp://ecmdb.ca/proteins/P23256.xml5-keto-4-deoxy-D-glucarate aldolaseP23522GARL_ECOLIgarLhttp://ecmdb.ca/proteins/P23522.xmlPhosphoenolpyruvate synthaseP23538PPSA_ECOLIppsAhttp://ecmdb.ca/proteins/P23538.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlLactaldehyde dehydrogenaseP25553ALDA_ECOLIaldAhttp://ecmdb.ca/proteins/P25553.xmlChorismate--pyruvate lyaseP26602UBIC_ECOLIubiChttp://ecmdb.ca/proteins/P26602.xmlNAD-dependent malic enzymeP26616MAO1_ECOLIsfcAhttp://ecmdb.ca/proteins/P26616.xmlAminodeoxychorismate lyaseP28305PABC_ECOLIpabChttp://ecmdb.ca/proteins/P28305.xmlL-serine dehydratase 2P30744SDHM_ECOLIsdaBhttp://ecmdb.ca/proteins/P30744.xml3-mercaptopyruvate sulfurtransferaseP31142THTM_ECOLIsseAhttp://ecmdb.ca/proteins/P31142.xmlMultiphosphoryl transfer protein 2P32670PTFX2_ECOLIptsAhttp://ecmdb.ca/proteins/P32670.xmlFormate acetyltransferase 2P32674PFLD_ECOLIpflDhttp://ecmdb.ca/proteins/P32674.xmlPyruvate formate-lyase 2-activating enzymeP32675PFLC_ECOLIpflChttp://ecmdb.ca/proteins/P32675.xmlL-lactate dehydrogenase [cytochrome]P33232LLDD_ECOLIlldDhttp://ecmdb.ca/proteins/P33232.xmlPTS system trehalose-specific EIIBC componentP36672PTTBC_ECOLItreBhttp://ecmdb.ca/proteins/P36672.xmlPhosphoenolpyruvate-protein phosphotransferase ptsPP37177PT1P_ECOLIptsPhttp://ecmdb.ca/proteins/P37177.xmlGalactitol-specific phosphotransferase enzyme IIB componentP37188PTKB_ECOLIgatBhttp://ecmdb.ca/proteins/P37188.xml2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthaseP37355MENH_ECOLImenHhttp://ecmdb.ca/proteins/P37355.xmlUncharacterized protein yjhHP39359YJHH_ECOLIyjhHhttp://ecmdb.ca/proteins/P39359.xmlL-serine dehydratase tdcGP42630TDCG_ECOLItdcGhttp://ecmdb.ca/proteins/P42630.xmlKeto-acid formate acetyltransferaseP42632TDCE_ECOLItdcEhttp://ecmdb.ca/proteins/P42632.xml4-hydroxy-2-oxovalerate aldolaseP51020HOA_ECOLImhpEhttp://ecmdb.ca/proteins/P51020.xmlD-lactate dehydrogenase_P52643LDHD_ECOLIldhAhttp://ecmdb.ca/proteins/P52643.xmlProbable pyruvate-flavodoxin oxidoreductaseP52647NIFJ_ECOLIydbKhttp://ecmdb.ca/proteins/P52647.xmlHeat-responsive suppressor hrsAP54745HRSA_ECOLIhrsAhttp://ecmdb.ca/proteins/P54745.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIB componentP56580PTHB_ECOLIsrlEhttp://ecmdb.ca/proteins/P56580.xmlPutative diaminopropionate ammonia-lyaseP66899DPAL_ECOLIygeXhttp://ecmdb.ca/proteins/P66899.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlPTS system mannose-specific EIIAB componentP69797PTNAB_ECOLImanXhttp://ecmdb.ca/proteins/P69797.xmlMultiphosphoryl transfer proteinP69811PTFAH_ECOLIfruBhttp://ecmdb.ca/proteins/P69811.xmlAscorbate-specific phosphotransferase enzyme IIA componentP69820ULAC_ECOLIulaChttp://ecmdb.ca/proteins/P69820.xmlAscorbate-specific phosphotransferase enzyme IIB componentP69822ULAB_ECOLIulaBhttp://ecmdb.ca/proteins/P69822.xmlGalactitol-specific phosphotransferase enzyme IIA componentP69828PTKA_ECOLIgatAhttp://ecmdb.ca/proteins/P69828.xmlUncharacterized protein yagEP75682YAGE_ECOLIyagEhttp://ecmdb.ca/proteins/P75682.xmlPutative formate acetyltransferase 3P75793PFLF_ECOLIybiWhttp://ecmdb.ca/proteins/P75793.xmlLow specificity L-threonine aldolaseP75823LTAE_ECOLIltaEhttp://ecmdb.ca/proteins/P75823.xmlD-malate dehydrogenase [decarboxylating]P76251DMLA_ECOLIdmlAhttp://ecmdb.ca/proteins/P76251.xmlD-cysteine desulfhydraseP76316DCYD_ECOLIdcyDhttp://ecmdb.ca/proteins/P76316.xml2-keto-3-deoxy-L-rhamnonate aldolaseP76469RHMA_ECOLIrhmAhttp://ecmdb.ca/proteins/P76469.xmlNADP-dependent malic enzymeP76558MAO2_ECOLImaeBhttp://ecmdb.ca/proteins/P76558.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlMultiphosphoryl transfer protein 1P77439PTFX1_ECOLIfryAhttp://ecmdb.ca/proteins/P77439.xmlCysteine desulfurase_P77444SUFS_ECOLIsufShttp://ecmdb.ca/proteins/P77444.xml1-deoxy-D-xylulose-5-phosphate synthaseP77488DXS_ECOLIdxshttp://ecmdb.ca/proteins/P77488.xmlMethylisocitrate lyaseP77541PRPB_ECOLIprpBhttp://ecmdb.ca/proteins/P77541.xmlThiosulfate sulfurtransferase YnjEP78067YNJE_ECOLIynjEhttp://ecmdb.ca/proteins/P78067.xml2-dehydro-3-deoxy-6-phosphogalactonate aldolaseQ6BF16DGOA_ECOLIdgoAhttp://ecmdb.ca/proteins/Q6BF16.xmlAscorbate-specific permease IIC component ulaAP39301ULAA_ECOLIulaAhttp://ecmdb.ca/proteins/P39301.xmlGlucitol/sorbitol permease IIC componentP56579PTHC_ECOLIsrlAhttp://ecmdb.ca/proteins/P56579.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlGalactitol permease IIC componentP69831PTKC_ECOLIgatChttp://ecmdb.ca/proteins/P69831.xmlUncharacterized protein ykgEP77252YKGE_ECOLIykgEhttp://ecmdb.ca/proteins/P77252.xmlUncharacterized aminotransferase yfbQP0A959YFBQ_ECOLIyfbQhttp://ecmdb.ca/proteins/P0A959.xmlFlavodoxin-2P0ABY4FLAW_ECOLIfldBhttp://ecmdb.ca/proteins/P0ABY4.xmlFlavodoxin-1P61949FLAV_ECOLIfldAhttp://ecmdb.ca/proteins/P61949.xmlPTS-dependent dihydroxyacetone kinase, dihydroxyacetone-binding subunit dhaKP76015DHAK_ECOLIdhaKhttp://ecmdb.ca/proteins/P76015.xmlUncharacterized protein ykgGP77433YKGG_ECOLIykgGhttp://ecmdb.ca/proteins/P77433.xmlUncharacterized electron transport protein ykgFP77536YKGF_ECOLIykgFhttp://ecmdb.ca/proteins/P77536.xmlPTS-dependent dihydroxyacetone kinase, ADP-binding subunit dhaLP76014DHAL_ECOLIdhaLhttp://ecmdb.ca/proteins/P76014.xmlPTS-dependent dihydroxyacetone kinase, phosphotransferase subunit dhaMP37349DHAM_ECOLIdhaMhttp://ecmdb.ca/proteins/P37349.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlAutonomous glycyl radical cofactorP68066GRCA_ECOLIgrcAhttp://ecmdb.ca/proteins/P68066.xmlUncharacterized aminotransferase yfdZP77434YFDZ_ECOLIyfdZhttp://ecmdb.ca/proteins/P77434.xmlPTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlPTS system beta-glucoside-specific EIIBCA componentP08722PTV3B_ECOLIbglFhttp://ecmdb.ca/proteins/P08722.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlPTS system maltose- and glucose-specific EIICB componentP19642PTOCB_ECOLImalXhttp://ecmdb.ca/proteins/P19642.xmlPTS system fructose-specific EIIBC componentP20966PTFBC_ECOLIfruAhttp://ecmdb.ca/proteins/P20966.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlPTS system trehalose-specific EIIBC componentP36672PTTBC_ECOLItreBhttp://ecmdb.ca/proteins/P36672.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlAscorbate-specific permease IIC component ulaAP39301ULAA_ECOLIulaAhttp://ecmdb.ca/proteins/P39301.xmlGlucitol/sorbitol permease IIC componentP56579PTHC_ECOLIsrlAhttp://ecmdb.ca/proteins/P56579.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlGalactitol permease IIC componentP69831PTKC_ECOLIgatChttp://ecmdb.ca/proteins/P69831.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlCoenzyme A + 2 flavodoxin semi oxidized + Pyruvic acid <> Acetyl-CoA + Carbon dioxide +2 Flavodoxin reduced + Hydrogen ionCoenzyme A + Pyruvic acid <> Acetyl-CoA + Formic acidR00212PYRUVFORMLY-RXNPhosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acidTRANS-RXN-167Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acid2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxideR08648ACETOOHBUTSYN-RXNHydrogen ion + 2 Pyruvic acid > (S)-2-Acetolactate + Carbon dioxideR00226Phosphoenolpyruvic acid + Arbutin > Arbutin 6-phosphate + Pyruvic acidTRANS-RXN-153Coenzyme A + NAD + Pyruvic acid > Acetyl-CoA + Carbon dioxide + NADHPYRUVDEH-RXNPhosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acidRXN0-2522L-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acidDihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXNChorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidR00986ANTHRANSYN-RXNL-Cystathionine + Water > L-Homocysteine + Ammonium + Pyruvic acidPhosphoenolpyruvic acid + D-Mannose > Mannose 6-phosphate + Pyruvic acidTRANS-RXN-165Phosphoenolpyruvic acid + D-Fructose > Fructose 6-phosphate + Pyruvic acidPhosphoenolpyruvic acid + N-Acetylmannosamine > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acidTRANS-RXN0-446Phosphoenolpyruvic acid + Glucosamine > Glucosamine 6-phosphate + Pyruvic acidTRANS-RXN-167AADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acidR00200PEPDEPHOS-RXNPhosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acidTRANS-RXN-161D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acidR00704DLACTDEHYDROGNAD-RXNPhosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acidalpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidR00258Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphateTRANS-RXN-169Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acidRXN0-2461Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acidPhosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphateTRANS-RXN-168Phosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphatePhosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acidD-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acidRXN0-5240Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-156L-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8L-Lactic acid + Menaquinone 8 > Menaquinol 8 + Pyruvic acidL-Cysteine + Water > Hydrogen sulfide + Ammonium + Pyruvic acidL-Serine > Ammonium + Pyruvic acidMethylisocitric acid <> Pyruvic acid + Succinic acidR00409METHYLISOCITRATE-LYASE-RXN4-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acidR00750MHPELY-RXND-Glyceraldehyde 3-phosphate + Hydrogen ion + Pyruvic acid <> Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphateR05636DXS-RXNWater + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acidR03037ISOCHORMAT-RXNWater + Pyruvic acid + Ubiquinone-8 > Acetic acid + Carbon dioxide + Ubiquinol-84-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acidR05553ADCLY-RXND-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acidL-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acidR00214MALIC-NAD-RXNAdenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + PhosphateR00199PEPSYNTH-RXN(R)-Malate + NAD <> Carbon dioxide + NADH + Pyruvic acidR002151.1.1.83-RXN2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acidR05605KDPGALDOL-RXNHydrogen ion + Oxalacetic acid > Carbon dioxide + Pyruvic acidOXALODECARB-RXND-Cysteine + Water > Hydrogen sulfide + Ammonium + Pyruvic acidD-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-82-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acidR08166RXN-9310D-Serine > Ammonium + Pyruvic acidPhosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acidTRANS-RXN-155BL-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acidR00216MALIC-NADP-RXNL-Aspartate-semialdehyde + Pyruvic acid > 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 WaterR02292DIHYDRODIPICSYN-RXNHydrogen cyanide + 3-Mercaptopyruvic acid + Cyanide <> Hydrogen ion + Pyruvic acid + ThiocyanateR03106MERCAPYSTRANS-RXN2,3-diaminopropionate + Water >2 Ammonium + Pyruvic acid5-Dehydro-4-deoxy-D-glucarate > Tartronate semialdehyde + Pyruvic acidR02754KDGALDOL-RXNN-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acidR01811ACNEULY-RXNalpha-Ketoisovaleric acid + L-Alanine <> Pyruvic acid + L-Valine + a-Ketoisovaleric acidR01215VALINE-PYRUVATE-AMINOTRANSFER-RXNWater + L-Tryptophan <> Indole + Ammonium + Pyruvic acidChorismate <> 4-Hydroxybenzoic acid + Pyruvic acidR01302CHORPYRLY-RXN2-Dehydro-3-deoxy-D-galactonate-6-phosphate <> D-Glyceraldehyde 3-phosphate + Pyruvic acidR01064DEHYDDEOXPHOSGALACT-ALDOL-RXN2-Acetolactate + Carbon dioxide <>2 Pyruvic acidR00006Pyruvic acid + Thiamine pyrophosphate <> 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxideR00014L-Lactic acid + 2 Ferricytochrome c + Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion + Ferrocytochrome cR00196Adenosine triphosphate + Pyruvic acid + Water <> Adenosine monophosphate + Phosphoenolpyruvic acid + PhosphateR00199PEPSYNTH-RXNAdenosine triphosphate + Pyruvic acid <> ADP + Phosphoenolpyruvic acidR00200Pyruvaldehyde + NAD + Water <> Pyruvic acid + NADH + Hydrogen ionR00203Acetyl-CoA + Formic acid <> Coenzyme A + Pyruvic acidR00212L-Malic acid + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ionR00214(R)-Malate + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ionR002151.1.1.83-RXNL-Malic acid + NADP <> Pyruvic acid + Carbon dioxide + NADPH + Hydrogen ionR00216MALIC-NADP-RXNL-Serine <> Pyruvic acid + AmmoniaR002204.3.1.17-RXND-Serine <> Pyruvic acid + AmmoniaR00221(S)-2-Acetolactate + Carbon dioxide <>2 Pyruvic acidR00226Guanosine triphosphate + Pyruvic acid <> Guanosine diphosphate + Phosphoenolpyruvic acidR004304-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acidR004704OH2OXOGLUTARALDOL-RXND-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acidR00471L-Tryptophan + Water <> Indole + Pyruvic acid + AmmoniaR00673TRYPTOPHAN-RXNAcetaldehyde + Pyruvic acid <> 4-Hydroxy-2-oxopentanoateR00750MHPELY-RXNL-Cysteine + Water <> Hydrogen sulfide + Pyruvic acid + AmmoniaR00782LCYSDESULF-RXNChorismate + Ammonia <> 2-Aminobenzoic acid + Pyruvic acid + WaterR00985Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR00986dATP + Pyruvic acid <> dADP + Phosphoenolpyruvic acidR011382 Reduced ferredoxin + Acetyl-CoA + Carbon dioxide + 2 Hydrogen ion + Oxidized ferredoxin <>2 Oxidized ferredoxin + Pyruvic acid + Coenzyme A + Reduced ferredoxinR01196L-Valine + Pyruvic acid <> alpha-Ketoisovaleric acid + L-AlanineR01215Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acidR01285L-Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acidR012864-Hydroxybenzoic acid + Pyruvic acid <> ChorismateR01302Pyruvic acid + Enzyme N6-(lipoyl)lysine <> [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Carbon dioxide + [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysineR01699N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acidR01811dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acidR01858D-Cysteine + Water <> Hydrogen sulfide + Ammonia + Pyruvic acidR018742-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-LactaldehydeR02261L-Aspartate-semialdehyde + Pyruvic acid <> 2,3-Dihydrodipicolinic acid +2 WaterR02292Nucleoside triphosphate + Pyruvic acid <> NDP + Phosphoenolpyruvic acidR02320L-Cystine + Water <> Pyruvic acid + Ammonia + ThiocysteineR024085-Dehydro-4-deoxy-D-glucarate <> Pyruvic acid + Tartronate semialdehydeR027542-Acetolactate + Thiamine pyrophosphate <> 2-(a-Hydroxyethyl)thiamine diphosphate + Pyruvic acidR030503-Mercaptopyruvic acid + Sulfite <> Thiosulfate + Pyruvic acidR03105Hydrogen cyanide + 3-Mercaptopyruvic acid <> Thiocyanate + Pyruvic acidR03106MERCAPYSTRANS-RXNPyruvic acid + Ubiquinone-1 + Water <> Acetic acid + Ubiquinol-8 + Carbon dioxideR03145Tartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarateR03277(S)-2-Acetolactate + Thiamine pyrophosphate <> 2-(a-Hydroxyethyl)thiamine diphosphate + Pyruvic acidR04672Selenocystathionine + Water <> Selenohomocysteine + Ammonia + Pyruvic acidR04941Propanal + Pyruvic acid <> 4-Hydroxy-2-oxohexanoic acidR052984-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acidR05553Pyruvic acid + D-Glyceraldehyde 3-phosphate <> 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxideR05636DXS-RXNPyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxideR08648Se-Methylselenocysteine + Water <> Pyruvic acid + Ammonia + MethaneselenolR09366an oxidized electron acceptor + L-Lactic acid > a reduced electron acceptor + Pyruvic acidL-LACTDEHYDROGFMN-RXNPyruvic acid + hydroxylamine > pyruvic oxime + WaterRXN-3482Hydrogen ion + Pyruvic acid + Acetaldehyde > acetoin + Carbon dioxideRXN0-2022Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acidRXN0-2461Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acidRXN0-2522D-Alanine + Pyridoxal 5'-phosphate <> Pyruvic acid + Pyridoxamine 5'-phosphateRXN0-5240Hydrogen ion + 3-Mercaptopyruvic acid > Pyruvic acid + Hydrogen sulfideRXN0-6945Arbutin + Phosphoenolpyruvic acid > Arbutin 6-phosphate + Pyruvic acidTRANS-RXN-153Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acidTRANS-RXN-157N-Acetylmannosamine + Phosphoenolpyruvic acid > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acidTRANS-RXN0-446NAD + (R)-Malate > NADH + Carbon dioxide + Pyruvic acid1.1.1.83-RXNDihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXN2,3-diaminopropanoate + Water > Hydrogen ion + Ammonia + Pyruvic acid4.3.1.15-RXNL-Serine > Hydrogen ion + Pyruvic acid + Ammonia4.3.1.17-RXN4-Hydroxy-2-oxoglutaric acid Glyoxylic acid + Pyruvic acid4OH2OXOGLUTARALDOL-RXNHydrogen ion + Pyruvic acid <> (<i>S</i>)-2-acetolactate + Carbon dioxideACETOLACTSYN-RXNOxoglutaric acid + L-Alanine <> L-Glutamate + Pyruvic acidALANINE-AMINOTRANSFERASE-RXNChorismate + L-Glutamine > Hydrogen ion + 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR00986ANTHRANSYN-RXNChorismate > 4-Hydroxybenzoic acid + Pyruvic acidR01302CHORPYRLY-RXNL-Cystathionine + Water > Hydrogen ion + Pyruvic acid + Ammonia + L-HomocysteineR01286CYSTATHIONINE-BETA-LYASE-RXNan electron-transfer-related quinone + Water + D-Alanine > an electron-transfer-related quinol + Ammonium + Pyruvic acidDALADEHYDROG-RXND-Cysteine + Water <> Pyruvic acid + Hydrogen sulfide + Ammonia + Hydrogen ionR01874DCYSDESULF-RXN2-Keto-3-deoxy-D-gluconic acid D-Glyceraldehyde + Pyruvic acidDHDOGALDOL-RXNPyruvic acid + L-Aspartate-semialdehyde <> Hydrogen ion + Water + 2,3-Dihydrodipicolinic acidDIHYDRODIPICSYN-RXNan electron-transfer-related quinone + D-Lactic acid > an electron-transfer-related quinol + Pyruvic acidDLACTDEHYDROGFAD-RXNNAD + D-Lactic acid < Hydrogen ion + NADH + Pyruvic acidDLACTDEHYDROGNAD-RXND-Serine > Hydrogen ion + Pyruvic acid + AmmoniaR00221DSERDEAM-RXNPyruvic acid + D-Glyceraldehyde 3-phosphate + Hydrogen ion > Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphateDXS-RXN2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acidKDPGALDOL-RXNL-Cysteine + Water > Pyruvic acid + Ammonia + Hydrogen sulfide + Hydrogen ionLCYSDESULF-RXNHydrogen cyanide + 3-Mercaptopyruvic acid Hydrogen ion + Pyruvic acid + ThiocyanateMERCAPYSTRANS-RXNMethylisocitric acid > Succinic acid + Pyruvic acidMETHYLISOCITRATE-LYASE-RXN4-Hydroxy-2-oxopentanoate <> Acetaldehyde + Pyruvic acidMHPELY-RXNPyruvic acid + Adenosine triphosphate <> Hydrogen ion + ADP + Phosphoenolpyruvic acidPEPDEPHOS-RXNWater + Pyruvic acid + Adenosine triphosphate > Hydrogen ion + Phosphate + Phosphoenolpyruvic acid + Adenosine monophosphatePEPSYNTH-RXNHydrogen ion + Pyruvic acid + Lipoamide S-Acetyldihydrolipoamide + Carbon dioxidePYRUVATEDECARB-RXNPyruvic acid + Coenzyme A + NAD > Acetyl-CoA + Carbon dioxide + NADHPYRUVDEH-RXNPyruvic acid + Water + a ubiquinone > Carbon dioxide + a ubiquinol + Acetic acidRXN-11496Hydrogen ion + Pyruvic acid + Thiamine pyrophosphate > 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxideR00014RXN-125832-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acidR08166RXN-9310Phosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acidRXN0-17Pyruvic acid + Hydrogen ion > L-Lactic acidRXN0-52692-keto-3-deoxy-L-rhamnonate Pyruvic acid + LactaldehydeRXN0-5433Acetic acid + Carbon dioxide + Hydrogen ion <> Pyruvic acid + WaterRXN0-6375Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acidTRANS-RXN-153APhosphoenolpyruvic acid + Cellobiose > Cellobiose-6-phosphate + Pyruvic acidTRANS-RXN-155Phosphoenolpyruvic acid + Chitobiose > Pyruvic acid + Diacetylchitobiose-6-phosphateTRANS-RXN-155BPhosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-156D-fructose + Phosphoenolpyruvic acid > Fructose 1-phosphate + Pyruvic acidTRANS-RXN-158D-fructose + Phosphoenolpyruvic acid > Fructose 6-phosphate + Pyruvic acidTRANS-RXN-158APhosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acidTRANS-RXN-161D-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acidTRANS-RXN-165Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acidTRANS-RXN-167Glucosamine + Phosphoenolpyruvic acid > Glucosamine 6-phosphate + Pyruvic acidTRANS-RXN-167APhosphoenolpyruvic acid + Trehalose > Trehalose 6-phosphate + Pyruvic acidTRANS-RXN-168Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-169L-Tryptophan + Water <> Hydrogen ion + Indole + Pyruvic acid + AmmoniaTRYPTOPHAN-RXNL-Alanine + Oxoglutaric acid > Pyruvic acid + L-Glutamate4-Hydroxy-2-oxoglutaric acid > Pyruvic acid + Glyoxylic acidL-Valine + Pyruvic acid > a-Ketoisovaleric acid + L-AlanineL-Aspartate-semialdehyde + Pyruvic acid > (S)-2,3-dihydrodipicolinate +2 WaterD-Cysteine + Water > Hydrogen sulfide + Ammonia + Pyruvic acid2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphatePhosphoenolpyruvic acid + protein L-histidine > Pyruvic acid + protein N(pi)-phospho-L-histidineD-Lactic acid + NAD > Pyruvic acid + NADH2,3-diaminopropionate + Water > Pyruvic acid +2 AmmoniaPyruvic acid + D-Glyceraldehyde 3-phosphate > 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxideIsochorismate + Water > 2,3-dihydroxy-2,3-dihydrobenzoate + Pyruvic acid2-Dehydro-3-deoxy-D-glucarate > Pyruvic acid + Tartronate semialdehyde2 Pyruvic acid > 2-Acetolactate + Carbon dioxideR00006Adenosine triphosphate + Pyruvic acid > ADP + Phosphoenolpyruvic acidL-Lactic acid + 2 Ferricytochrome c > Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ionL-Cystathionine + Water > L-Homocysteine + Ammonia + Pyruvic acidN-acetylneuraminate > N-Acetylmannosamine + Pyruvic acidPyruvic acid + CoA + oxidized flavodoxin > Acetyl-CoA + Carbon dioxide + reduced flavodoxinPyruvic acid + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine > [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Carbon dioxide4-Amino-4-deoxychorismate > p-Aminobenzoic acid + Pyruvic acidAcetyl-CoA + Formic acid > CoA + Pyruvic acidPyruvic acid + Ubiquinone-10 + Water > Acetic acid + Carbon dioxide + Ubiquinol-1Adenosine triphosphate + Pyruvic acid + Water > Adenosine monophosphate + Phosphoenolpyruvic acid + Inorganic phosphate(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate > Pyruvic acid + Succinic acid2-Dehydro-3-deoxy-L-rhamnonate > Pyruvic acid + D-LactaldehydeD-Serine > Pyruvic acid + AmmoniaL-Serine > Pyruvic acid + AmmoniaR002204.3.1.17-RXN3-Mercaptopyruvic acid + Hydrogen cyanide > Pyruvic acid + ThiocyanateL-Tryptophan + Water > Indole + Pyruvic acid + AmmoniaChorismate + L-Glutamine > 2-Aminobenzoic acid + Pyruvic acid + L-GlutamatePyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + WaterR10147 L-Cystathionine + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> L-Homocysteine + Pyruvic acid + AmmoniaR01286 L-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + AmmoniaR00220 D-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + AmmoniaR00221 Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidineR02628 2,3-Diaminopropanoate + Water <> Pyruvic acid +2 AmmoniaR00195 L-Tryptophan + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> Indole + Pyruvic acid + AmmoniaR00673 L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADHR00214 L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPHR00216 D-Glyceraldehyde 3-phosphate + Pyruvic acid + Hydrogen ion + D-Glyceraldehyde 3-phosphate > 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphatePW_R003330Water + isochorismate + Isochorismate > Pyruvic acid + 2,3-dihydroxy-2,3-dihydrobenzoatePW_R002453L-Aspartate-semialdehyde + Pyruvic acid > Hydrogen ion + Water + (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinatePW_R002527Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate > Adenosine diphosphate + Phosphate + Oxalacetic acid + ADPPW_R002581L-Alanine + Oxoglutaric acid + L-Alanine <> L-Glutamic acid + Pyruvic acid + L-GlutamatePW_R002586L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acidPW_R002587Phosphoenolpyruvic acid + Adenosine monophosphate + Phosphate + 2 Hydrogen ion > Adenosine triphosphate + Water + Pyruvic acidPW_R002640Water + Adenosine triphosphate + Pyruvic acid > Adenosine monophosphate + Phosphate +2 Hydrogen ion + Phosphoenolpyruvic acidPW_R003675Phosphoenolpyruvic acid + Adenosine diphosphate + Hydrogen ion + ADP > Adenosine triphosphate + Pyruvic acidPW_R002641Pyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Alanine + L-AlaninePW_R002660L-Valine + Pyruvic acid + L-Valine > L-Alanine + a-Ketoisovaleric acid + L-AlaninePW_R002662D-Alanine + Water + Quinone > Ammonium + Pyruvic acid + HydroquinonePW_R002664D-Alanine + Water + an electron-transfer quinone > Ammonium + Pyruvic acid + electron-transfer quinolPW_R0037335-dehydro-4-deoxy-D-glucarate(2−) > Pyruvic acid + Tartronate semialdehydePW_R002725Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-GlutamatePW_R002894L-Malic acid + NADP + L-Malic acid > Carbon dioxide + NADPH + Pyruvic acid + NADPHPW_R002930L-Malic acid + NAD + L-Malic acid > Carbon dioxide + NADH + Pyruvic acidPW_R0029312-dehydro-3-deoxy-D-galactonate 6-phosphate + 2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphatePW_R002942L-Lactic acid + oxidized electron acceptor + L-Lactic acid > Reduced acceptor + Pyruvic acidPW_R0029782-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphatePW_R0030654-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acidPW_R0034024-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + AcetaldehydePW_R0051622-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylatePW_R005216Pyruvic acid > Carbon dioxide + 2-AcetolactatePW_R005828L-Lactic acid + oxidized electron acceptor > Pyruvic acid + reduced electron acceptorPW_R006056N-Acetylneuraminic acid > Pyruvic acid + N-AcetylmannosaminePW_R0059363-Mercaptopyruvic acid > Pyruvic acid + Hydrogen sulfidePW_R006040Pyruvic acid + a [pyruvate dehydrogenase E2 protein] N6-lipoyl-L-lysine + Hydrogen ion > a [pyruvate dehydrogenase E2 protein] N6-S-acetyldihydrolipoyl-L-lysine + Carbon dioxidePW_R006082D-Lactic acid + 2 Hydrogen ion + an ubiquinol > Pyruvic acid + ubiquinonePW_R006087L-Lactic acid + Ubiquinone-6 > Pyruvic acid + Ubiquinol-6PW_R0061512 Pyruvic acid + 2 Water > Carbon dioxide + Acetic acid + Hydrogen ion + ElectronPW_R006089Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidineChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + Ammonia <>2 2-Aminobenzoic acid + Pyruvic acid + WaterMethylisocitric acid <> Pyruvic acid + Succinic acidD-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acidL-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 WaterL-Serine <> Pyruvic acid + AmmoniaADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acidAdenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + Phosphatealpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid4 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acidD-Serine <> Pyruvic acid + AmmoniaL-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acidD-Glyceraldehyde 3-phosphate + Hydrogen ion + Pyruvic acid <> Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphatePyruvic acid + D-Glyceraldehyde 3-phosphate <> 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide2 2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxideL-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ionL-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acidPyruvic acid + Ubiquinone-1 + Water <> Acetic acid + Ubiquinol-8 + Carbon dioxideChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidMethylisocitric acid <> Pyruvic acid + Succinic acidD-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acidL-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 WaterL-Serine <> Pyruvic acid + AmmoniaADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acidalpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidD-Glyceraldehyde 3-phosphate + Hydrogen ion + Pyruvic acid <> Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate2 2-Ketobutyric acid + Hydrogen ion + Pyruvic acid >2 2-Aceto-2-hydroxy-butyrate + Carbon dioxide2 2-Acetolactate + Carbon dioxide <>2 Pyruvic acidalpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acidL-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ionPyruvic acid + Enzyme N6-(lipoyl)lysine <> [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Carbon dioxidePyruvic acid + Ubiquinone-1 + Water <> Acetic acid + Ubiquinol-8 + Carbon dioxideL-Serine <> Pyruvic acid + Ammonia4.0 g/L Na2SO4; 5.36 g/L (NH4)2SO4; 1.0 g/L NH4Cl; 7.3 g/L K2HPO4; 1.8 g/L NaH2PO4 H2O; 12.0 g/L (NH4)2-H-citrate; 4.0 mL/L MgSO4 (1 M); 6.0 mL/L trace element solution; 0.02 g/L thiamine, 20 g/L glucoseBioreactor, pH controlled, aerated, dilution rate=0.125 L/h8050.0uM0.037 oCW3110Mid Log Phase322000000Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.900.0uM0.0K-12360000001. Cybercell Database: <a href='http://ccdb.wishartlab.com/CCDB/cgi-bin/STAT_NEW.cgi'>http://ccdb.wishartlab.com/CCDB/cgi-bin/STAT_NEW.cgi</a> <br>
2. Phillips R., Kondev, J., Theriot, J. (2008) “Physical Biology of the Cell” Garland Science, New York, NY.