2.02012-05-31 10:25:12 -06002015-09-13 12:56:07 -0600ECMDB00263M2MDB000111Phosphoenolpyruvic acidPhosphoenolpyruvate (PEP) plays a key role in many metabolic reactions. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia) 2-Hydroxy-Acrylate dihydrogen phosphate2-Hydroxy-Acrylic acid dihydrogen phosphate2-Hydroxy-acrylic acid dihydrogen phosphoric acid2-Phosphonooxyprop-2-enoate2-Phosphonooxyprop-2-enoic acidP-<i>enol</i>-pyrP-<i>enol</i>-pyruvateP-Enol-pyrP-Enol-pyruvateP-Enol-pyruvic acidPEPPhosphoenolpyruvateC3H5O6P168.042167.9823744042-(phosphonooxy)prop-2-enoic acidphosphoenolpyruvic acid138-08-9OC(=O)C(=C)OP(O)(O)=OInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)DTBNBXWJWCWCIK-UHFFFAOYSA-NSolidCytosollogp-1.22logs-1.10solubility1.32e+01 g/llogp-0.64pka_strongest_acidic0.76iupac2-(phosphonooxy)prop-2-enoic acidaverage_mass168.042mono_mass167.982374404smilesOC(=O)C(=C)OP(O)(O)=OformulaC3H5O6PinchiInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)inchikeyDTBNBXWJWCWCIK-UHFFFAOYSA-Npolar_surface_area104.06refractivity30.13polarizability11.57rotatable_bond_count3acceptor_count5donor_count3physiological_charge-3formal_charge0Citrate cycle (TCA cycle)ec00020Reductive carboxylate cycle (CO2 fixation)ec00720Purine metabolismec00230Phenylalanine, tyrosine and tryptophan biosynthesisec00400Carbon fixation in photosynthetic organismsec00710Glycolysis / Gluconeogenesisec00010Amino sugar and nucleotide sugar metabolismec00520Pyruvate metabolismec00620Methane metabolismec00680Peptidoglycan biosynthesisec00550Lipopolysaccharide biosynthesisE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831ec00540MetabolicMicrobial metabolism in diverse environmentsec01120Phosphonate and phosphinate metabolismec00440Phosphotransferase system (PTS)ec02060Metabolic pathwayseco01100Amino sugar and nucleotide sugar metabolism IThe synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate.
N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively.
Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate.
N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate.
UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens.
UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism.
PW000886MetabolicChorismate biosynthesisChorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway is catalyzed by three separate enzymes, all involved in the biosynthesis of Shikimic acid, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent.
The biosynthesis of chorismate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving Quinate/shikimate dehydrogenase and shikimate dehydrogenase 2. Shikimic acid is phosphorylated by Shikimate kinase 2 into shikimate 3-phosphate. Shikimate 3- phophate and a phosphoenolpyruvic acid are then joined through a 3-phosphoshikimate 1-carboxyvinyltransferase to produce a 5-enoylpyruvyl-shikimate 3-phosphate while releasing a phosphate. This in turns produces our final product Chorismate through a chorismate synthase. PW000816MetabolicGluconeogenesis 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.
PW000819MetabolicSecondary Metabolites: Shikimate PathwayThe biosynthesis of shikimate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving an NADPH driven Quinate/shikimate dehydrogenase or a NADPH driven shikimate dehydrogenase 2.
Shikimate can also be transported through a shikimate:H+ symporter.PW000985Metabolicfructose 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.
PW000913Metabolicglycerol 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.
PW000785Metabolicpeptidoglycan biosynthesis IPeptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space.
The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.
PW000906Metabolicsuperpathway 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.PW000795Metaboliclipopolysaccharide biosynthesis IIE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA. A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and CMP-3-deoxy-α-D-manno-octulosonate. CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound can either interact with a phosphoethanolamine resulting in a 1,2-diacyl-sn-glycerol and a phosphoethanolamine-Kdo2-lipid A which can be exported outside the cell, or it can interact with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core. A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter. The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface.PW001905Metaboliclipopolysaccharide biosynthesis IIIE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound can either react with a palmitoleoyl-acp through a palmitoleoyl acyltransferase resulting in the release of a holo-acyl carriere protein and a Kdo2-palmitoleoyl-lipid IVa which in turn reacts with a myristoyl-acp through a myristoyl-acp dependent acyltransferase resulting in a release of a holo-acp and a Kdo2-lipid A, cold adapted, or it can interact with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW002059Metabolicpeptidoglycan biosynthesis I 2Peptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space. The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.PW002062Metabolicmixed acid fermentationFERMENTATION-PWYgluconeogenesis IGLUCONEO-PWYglycolysis IGLYCOLYSISrespiration (anaerobic)ANARESP1-PWYCMP-KDO biosynthesis IPWY-1269glycerol degradation VGLYCEROLMETAB-PWYUDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing)PWY-6387chorismate biosynthesis from 3-dehydroquinatePWY-61633-dehydroquinate biosynthesis IPWY-6164Specdb::CMs505Specdb::CMs2960Specdb::CMs30667Specdb::CMs37391Specdb::CMs168410Specdb::CMs1056381Specdb::CMs1056382Specdb::CMs1056384Specdb::NmrOneD1298Specdb::NmrOneD4820Specdb::NmrOneD4821Specdb::NmrOneD6342Specdb::NmrOneD6343Specdb::NmrOneD6344Specdb::NmrOneD6345Specdb::NmrOneD6346Specdb::NmrOneD6347Specdb::NmrOneD6348Specdb::NmrOneD6349Specdb::NmrOneD6350Specdb::NmrOneD6351Specdb::NmrOneD6352Specdb::NmrOneD6353Specdb::NmrOneD6354Specdb::NmrOneD6355Specdb::NmrOneD6356Specdb::NmrOneD6357Specdb::NmrOneD6358Specdb::NmrOneD6359Specdb::NmrOneD6360Specdb::NmrOneD6361Specdb::MsMs457Specdb::MsMs458Specdb::MsMs459Specdb::MsMs3822Specdb::MsMs3823Specdb::MsMs3824Specdb::MsMs3825Specdb::MsMs3826Specdb::MsMs3827Specdb::MsMs3828Specdb::MsMs3829Specdb::MsMs3830Specdb::MsMs3831Specdb::MsMs3832Specdb::MsMs3833Specdb::MsMs3834Specdb::MsMs3835Specdb::MsMs3836Specdb::MsMs3837Specdb::MsMs3838Specdb::MsMs3839Specdb::MsMs3840Specdb::MsMs3841Specdb::MsMs3842Specdb::MsMs3843Specdb::NmrTwoD1010Specdb::NmrTwoD1246HMDB002631005980C0007426055PHOSPHO-ENOL-PYRUVATEPEPPEPKeseler, I. 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"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 80:2939-2948.18331064Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23.15158257Park, 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.Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Nakayama 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):18.15882454Krogh P: Role of ochratoxin in disease causation. Food Chem Toxicol. 1992 Mar;30(3):213-24.1618445Germaine GR, Tellefson LM: Promotion of Streptococcus mutans glucose transport by human whole saliva and parotid fluid. Infect Immun. 1985 Apr;48(1):7-13.3980096Schatzberger P: Maternity services. BMJ. 1992 May 23;304(6838):1382-3.1611358Orye E, Verhaaren H, Samuel K, van Mele B: A 46,XX,10Q+ chromosome constitution in a girl. Partial long arm duplication or insertional translocation? Humangenetik. 1975 May 26;28(1):1-8.1150258Landau BR, Chandramouli V, Schumann WC, Ekberg K, Kumaran K, Kalhan SC, Wahren J: Estimates of Krebs cycle activity and contributions of gluconeogenesis to hepatic glucose production in fasting healthy subjects and IDDM patients. Diabetologia. 1995 Jul;38(7):831-8.7556986Shirokane Y, Nakajima M, Mizusawa K: A new enzymatic assay of urinary guanidinoacetic acid. Clin Chim Acta. 1991 Oct 31;202(3):227-36.1667626Tannen RL: Ammonia metabolism. Am J Physiol. 1978 Oct;235(4):F265-77.29492Atkin BM, Buist NR, Utter MF, Leiter AB, Banker BQ: Pyruvate carboxylase deficiency and lactic acidosis in a retarded child without Leigh's disease. Pediatr Res. 1979 Feb;13(2):109-16.219411Bojarska-Dahlig H, Gloabski T, Dzioegielewska I: [Salts of cyclic erythromycin A carbonate with cinnamic acid derivatives] Acta Pol Pharm. 1975;32(3):311-7.1155186Matsumoto T, van der Auwera P, Watanabe Y, Tanaka M, Ogata N, Naito S, Kumazawa J: Neutrophil function in hyperosmotic NaCl is preserved by phosphoenol pyruvate. Urol Res. 1991;19(4):223-7.1656579Cahill GF Jr, Aoki TT: Renal gluconeogenesis and amino-acid metabolism in man. Med Clin North Am. 1975 May;59(3):751-61.1092934Beyer C: Creatine measurement in serum and urine with an automated enzymatic method. Clin Chem. 1993 Aug;39(8):1613-9.8353946Momeni N, Yoshimoto T, Ryberg B, Sandberg-Wollheim M, Grubb A: Factors influencing analysis of prolyl endopeptidase in human blood and cerebrospinal fluid: increase in assay sensitivity. Scand J Clin Lab Invest. 2003;63(6):387-95.14594319Simon, Ethan S.; Grabowski, Sven; Whitesides, George M. Preparation of phosphoenolpyruvate from D-(-)-3-phosphoglyceric acid for use in regeneration of ATP. Journal of the American Chemical Society (1989), 111(24), 8920-1.http://hmdb.ca/system/metabolites/msds/000/000/194/original/HMDB00263.pdf?1358461904PTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlPhosphoenolpyruvate carboxylaseP00864CAPP_ECOLIppchttp://ecmdb.ca/proteins/P00864.xmlPhospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitiveP00887AROH_ECOLIaroHhttp://ecmdb.ca/proteins/P00887.xmlPhospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitiveP00888AROF_ECOLIaroFhttp://ecmdb.ca/proteins/P00888.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIA componentP05706PTHA_ECOLIsrlBhttp://ecmdb.ca/proteins/P05706.xmlPTS system beta-glucoside-specific EIIBCA componentP08722PTV3B_ECOLIbglFhttp://ecmdb.ca/proteins/P08722.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xml3-phosphoshikimate 1-carboxyvinyltransferaseP0A6D3AROA_ECOLIaroAhttp://ecmdb.ca/proteins/P0A6D3.xmlEnolaseP0A6P9ENO_ECOLIenohttp://ecmdb.ca/proteins/P0A6P9.xml2-dehydro-3-deoxyphosphooctonate aldolaseP0A715KDSA_ECOLIkdsAhttp://ecmdb.ca/proteins/P0A715.xmlUDP-N-acetylglucosamine 1-carboxyvinyltransferaseP0A749MURA_ECOLImurAhttp://ecmdb.ca/proteins/P0A749.xmlPhospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitiveP0AB91AROG_ECOLIaroGhttp://ecmdb.ca/proteins/P0AB91.xmlPyruvate kinase IP0AD61KPYK1_ECOLIpykFhttp://ecmdb.ca/proteins/P0AD61.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.xmlPhosphoenolpyruvate carboxykinase [ATP]P22259PCKA_ECOLIpckAhttp://ecmdb.ca/proteins/P22259.xmlPhosphoenolpyruvate synthaseP23538PPSA_ECOLIppsAhttp://ecmdb.ca/proteins/P23538.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlMultiphosphoryl transfer protein 2P32670PTFX2_ECOLIptsAhttp://ecmdb.ca/proteins/P32670.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.xmlHeat-responsive suppressor hrsAP54745HRSA_ECOLIhrsAhttp://ecmdb.ca/proteins/P54745.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIB componentP56580PTHB_ECOLIsrlEhttp://ecmdb.ca/proteins/P56580.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.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlMultiphosphoryl transfer protein 1P77439PTFX1_ECOLIfryAhttp://ecmdb.ca/proteins/P77439.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.xmlPTS-dependent dihydroxyacetone kinase, dihydroxyacetone-binding subunit dhaKP76015DHAK_ECOLIdhaKhttp://ecmdb.ca/proteins/P76015.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.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.xmlPhosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acidTRANS-RXN-167Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acidPhosphoenolpyruvic acid + Arbutin > Arbutin 6-phosphate + Pyruvic acidTRANS-RXN-153Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acidRXN0-2522Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXNPhosphoenolpyruvic 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-161Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acidPhosphoenolpyruvic 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-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + PhosphateR01826DAHPSYN-RXNPhosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acidTRANS-RXN-156Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + PhosphateR034602.5.1.19-RXND-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <> 3-Deoxy-D-manno-octulosonate 8-phosphate + PhosphateR03254KDO-8PSYNTH-RXNAdenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + PhosphateR00199PEPSYNTH-RXNPhosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acidTRANS-RXN-155B2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acidR006582PGADEHYDRAT-RXNPhosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamineR00660UDPNACETYLGLUCOSAMENOLPYRTRANS-RXNAdenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acidR00341PEPCARBOXYKIN-RXNCarbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonateR00345Adenosine triphosphate + Pyruvic acid + Water <> Adenosine monophosphate + Phosphoenolpyruvic acid + PhosphateR00199PEPSYNTH-RXNAdenosine triphosphate + Pyruvic acid <> ADP + Phosphoenolpyruvic acidR00200Phosphate + Oxalacetic acid <> Water + Phosphoenolpyruvic acid + Carbon dioxideR00345Guanosine triphosphate + Pyruvic acid <> Guanosine diphosphate + Phosphoenolpyruvic acidR00430dATP + Pyruvic acid <> dADP + Phosphoenolpyruvic acidR01138dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acidR01858Nucleoside triphosphate + Pyruvic acid <> NDP + Phosphoenolpyruvic acidR023203-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate <> Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + WaterR03254Phosphoenolpyruvic 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 acidRXN0-2522Arbutin + 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-RXN0-446Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXND-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid > 3-Deoxy-D-manno-octulosonate 8-phosphate + PhosphateKDO-8PSYNTH-RXNPhosphate + Oxalacetic acid <> Phosphoenolpyruvic acid + Hydrogen carbonatePEPCARBOX-RXNOxalacetic acid + Adenosine triphosphate > Carbon dioxide + Phosphoenolpyruvic acid + ADPPEPCARBOXYKIN-RXNPyruvic acid + Adenosine triphosphate <> Hydrogen ion + ADP + Phosphoenolpyruvic acidPEPDEPHOS-RXNWater + Pyruvic acid + Adenosine triphosphate > Hydrogen ion + Phosphate + Phosphoenolpyruvic acid + Adenosine monophosphatePEPSYNTH-RXNPhosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acidRXN0-17Phosphoenolpyruvic 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-169Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + PhosphateUDPNACETYLGLUCOSAMENOLPYRTRANS-RXNPhosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimatePhosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphateInorganic phosphate + Oxalacetic acid > Water + Phosphoenolpyruvic acid + Carbonic acidPhosphoenolpyruvic acid + protein L-histidine > Pyruvic acid + protein N(pi)-phospho-L-histidine2-Phospho-D-glyceric acid > Phosphoenolpyruvic acid + WaterPhosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water > 3-Deoxy-D-manno-octulosonate 8-phosphate + Inorganic phosphateAdenosine triphosphate + Pyruvic acid > ADP + Phosphoenolpyruvic acidPhosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine > Inorganic phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamineAdenosine triphosphate + Pyruvic acid + Water > Adenosine monophosphate + Phosphoenolpyruvic acid + Inorganic phosphatePhosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidineR02628 Phosphoenolpyruvic acid > Water + 2-Phosphoglyceric acid + 2-Phosphoglyceric acidPW_R0029322-Phosphoglyceric acid + 2-Phosphoglyceric acid <> Water + Phosphoenolpyruvic acidPW_R003674Phosphoenolpyruvic 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_R002641D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphatePW_R002910shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphatePW_R002916Oxalacetic acid + Adenosine triphosphate > Adenosine diphosphate + Carbon dioxide + Phosphoenolpyruvic acid + ADPPW_R002929D-Arabinose 5-phosphate + Phosphoenolpyruvic acid + Water > Phosphate + 3-deoxy-D-manno-octulosonate 8-phosphate + 3-Deoxy-D-manno-octulosonate 8-phosphatePW_R003031Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > Phosphate + UDP-N-acetyl-α-D-glucosamine-enolpyruvatePW_R003317Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidineADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acidD-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + PhosphateAdenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + Phosphate2 2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acidD-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + PhosphateCarbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonatePhosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamineAdenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acidADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acidD-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + PhosphateD-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate4.0 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, aerated10.9uM0.037 oCW3110Stationary Phase436000Park, 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.M9 Minimal Media, 4 g/L GlucoseBioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h70.0uM6.037 oCBW25113Mid-Log Phase28000024000Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23.15158257Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture184.0uM0.037 oCK12 NCM3722Mid-Log Phase7360000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolShake flask and filter culture1340.0uM0.037 oCK12 NCM3722Mid-Log Phase53600000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateShake flask and filter culture909.0uM0.037 oCK12 NCM3722Mid-Log Phase36360000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621