2.0 2012-05-31 10:25:12 -0600 2015-09-13 12:56:07 -0600 ECMDB00263 M2MDB000111 Phosphoenolpyruvic acid Phosphoenolpyruvate (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 phosphate 2-Hydroxy-Acrylic acid dihydrogen phosphate 2-Hydroxy-acrylic acid dihydrogen phosphoric acid 2-Phosphonooxyprop-2-enoate 2-Phosphonooxyprop-2-enoic acid P-<i>enol</i>-pyr P-<i>enol</i>-pyruvate P-Enol-pyr P-Enol-pyruvate P-Enol-pyruvic acid PEP Phosphoenolpyruvate C3H5O6P 168.042 167.982374404 2-(phosphonooxy)prop-2-enoic acid phosphoenolpyruvic acid 138-08-9 OC(=O)C(=C)OP(O)(O)=O InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) DTBNBXWJWCWCIK-UHFFFAOYSA-N Solid Cytosol logp -1.22 ALOGPS logs -1.10 ALOGPS solubility 1.32e+01 g/l ALOGPS logp -0.64 ChemAxon pka_strongest_acidic 0.76 ChemAxon iupac 2-(phosphonooxy)prop-2-enoic acid ChemAxon average_mass 168.042 ChemAxon mono_mass 167.982374404 ChemAxon smiles OC(=O)C(=C)OP(O)(O)=O ChemAxon formula C3H5O6P ChemAxon inchi InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) ChemAxon inchikey DTBNBXWJWCWCIK-UHFFFAOYSA-N ChemAxon polar_surface_area 104.06 ChemAxon refractivity 30.13 ChemAxon polarizability 11.57 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Citrate cycle (TCA cycle) ec00020 Reductive carboxylate cycle (CO2 fixation) ec00720 Purine metabolism ec00230 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Carbon fixation in photosynthetic organisms ec00710 Glycolysis / Gluconeogenesis ec00010 Amino sugar and nucleotide sugar metabolism ec00520 Pyruvate metabolism ec00620 Methane metabolism ec00680 Peptidoglycan biosynthesis ec00550 Lipopolysaccharide biosynthesis E. 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. PW000831 ec00540 Metabolic Microbial metabolism in diverse environments ec01120 Phosphonate and phosphinate metabolism ec00440 Phosphotransferase system (PTS) ec02060 Metabolic pathways eco01100 Amino sugar and nucleotide sugar metabolism I The 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. PW000886 Metabolic Chorismate biosynthesis Chorismate 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. PW000816 Metabolic Gluconeogenesis from L-malic acid Gluconeogenesis 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. PW000819 Metabolic Secondary Metabolites: Shikimate Pathway The 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. PW000985 Metabolic fructose metabolism Fructose 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. PW000913 Metabolic glycerol metabolism 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 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. PW000914 Metabolic glycerol metabolism II 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-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. PW000915 Metabolic glycerol 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. PW000916 Metabolic glycerol 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. PW000917 Metabolic glycerol 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. PW000918 Metabolic glycolysis and pyruvate dehydrogenase Fructose 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. PW000785 Metabolic peptidoglycan biosynthesis I Peptidoglycan 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. PW000906 Metabolic superpathway 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. PW000795 Metabolic lipopolysaccharide biosynthesis II E. 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. PW001905 Metabolic lipopolysaccharide biosynthesis III E. 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. PW002059 Metabolic peptidoglycan biosynthesis I 2 Peptidoglycan 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. PW002062 Metabolic mixed acid fermentation FERMENTATION-PWY gluconeogenesis I GLUCONEO-PWY glycolysis I GLYCOLYSIS respiration (anaerobic) ANARESP1-PWY CMP-KDO biosynthesis I PWY-1269 glycerol degradation V GLYCEROLMETAB-PWY UDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing) PWY-6387 chorismate biosynthesis from 3-dehydroquinate PWY-6163 3-dehydroquinate biosynthesis I PWY-6164 Specdb::CMs 505 Specdb::CMs 2960 Specdb::CMs 30667 Specdb::CMs 37391 Specdb::CMs 168410 Specdb::CMs 1056381 Specdb::CMs 1056382 Specdb::CMs 1056384 Specdb::NmrOneD 1298 Specdb::NmrOneD 4820 Specdb::NmrOneD 4821 Specdb::NmrOneD 6342 Specdb::NmrOneD 6343 Specdb::NmrOneD 6344 Specdb::NmrOneD 6345 Specdb::NmrOneD 6346 Specdb::NmrOneD 6347 Specdb::NmrOneD 6348 Specdb::NmrOneD 6349 Specdb::NmrOneD 6350 Specdb::NmrOneD 6351 Specdb::NmrOneD 6352 Specdb::NmrOneD 6353 Specdb::NmrOneD 6354 Specdb::NmrOneD 6355 Specdb::NmrOneD 6356 Specdb::NmrOneD 6357 Specdb::NmrOneD 6358 Specdb::NmrOneD 6359 Specdb::NmrOneD 6360 Specdb::NmrOneD 6361 Specdb::MsMs 457 Specdb::MsMs 458 Specdb::MsMs 459 Specdb::MsMs 3822 Specdb::MsMs 3823 Specdb::MsMs 3824 Specdb::MsMs 3825 Specdb::MsMs 3826 Specdb::MsMs 3827 Specdb::MsMs 3828 Specdb::MsMs 3829 Specdb::MsMs 3830 Specdb::MsMs 3831 Specdb::MsMs 3832 Specdb::MsMs 3833 Specdb::MsMs 3834 Specdb::MsMs 3835 Specdb::MsMs 3836 Specdb::MsMs 3837 Specdb::MsMs 3838 Specdb::MsMs 3839 Specdb::MsMs 3840 Specdb::MsMs 3841 Specdb::MsMs 3842 Specdb::MsMs 3843 Specdb::NmrTwoD 1010 Specdb::NmrTwoD 1246 HMDB00263 1005 980 C00074 26055 PHOSPHO-ENOL-PYRUVATE PEP PEP Keseler, I. 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Am J Physiol. 1978 Oct;235(4):F265-77. 29492 Atkin 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. 219411 Bojarska-Dahlig H, Gloabski T, Dzioegielewska I: [Salts of cyclic erythromycin A carbonate with cinnamic acid derivatives] Acta Pol Pharm. 1975;32(3):311-7. 1155186 Matsumoto 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. 1656579 Cahill GF Jr, Aoki TT: Renal gluconeogenesis and amino-acid metabolism in man. Med Clin North Am. 1975 May;59(3):751-61. 1092934 Beyer C: Creatine measurement in serum and urine with an automated enzymatic method. Clin Chem. 1993 Aug;39(8):1613-9. 8353946 Momeni 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. 14594319 Simon, 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?1358461904 PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Phosphoenolpyruvate carboxylase P00864 CAPP_ECOLI ppc http://ecmdb.ca/proteins/P00864.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitive P00887 AROH_ECOLI aroH http://ecmdb.ca/proteins/P00887.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitive P00888 AROF_ECOLI aroF http://ecmdb.ca/proteins/P00888.xml Glucitol/sorbitol-specific phosphotransferase enzyme IIA component P05706 PTHA_ECOLI srlB http://ecmdb.ca/proteins/P05706.xml PTS system beta-glucoside-specific EIIBCA component P08722 PTV3B_ECOLI bglF http://ecmdb.ca/proteins/P08722.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml 3-phosphoshikimate 1-carboxyvinyltransferase P0A6D3 AROA_ECOLI aroA http://ecmdb.ca/proteins/P0A6D3.xml Enolase P0A6P9 ENO_ECOLI eno http://ecmdb.ca/proteins/P0A6P9.xml 2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI kdsA http://ecmdb.ca/proteins/P0A715.xml UDP-N-acetylglucosamine 1-carboxyvinyltransferase P0A749 MURA_ECOLI murA http://ecmdb.ca/proteins/P0A749.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive P0AB91 AROG_ECOLI aroG http://ecmdb.ca/proteins/P0AB91.xml Pyruvate kinase I P0AD61 KPYK1_ECOLI pykF http://ecmdb.ca/proteins/P0AD61.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml PTS system fructose-specific EIIBC component P20966 PTFBC_ECOLI fruA http://ecmdb.ca/proteins/P20966.xml Pyruvate kinase II P21599 KPYK2_ECOLI pykA http://ecmdb.ca/proteins/P21599.xml Phosphoenolpyruvate carboxykinase [ATP] P22259 PCKA_ECOLI pckA http://ecmdb.ca/proteins/P22259.xml Phosphoenolpyruvate synthase P23538 PPSA_ECOLI ppsA http://ecmdb.ca/proteins/P23538.xml PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml Multiphosphoryl transfer protein 2 P32670 PTFX2_ECOLI ptsA http://ecmdb.ca/proteins/P32670.xml PTS system trehalose-specific EIIBC component P36672 PTTBC_ECOLI treB http://ecmdb.ca/proteins/P36672.xml Phosphoenolpyruvate-protein phosphotransferase ptsP P37177 PT1P_ECOLI ptsP http://ecmdb.ca/proteins/P37177.xml Galactitol-specific phosphotransferase enzyme IIB component P37188 PTKB_ECOLI gatB http://ecmdb.ca/proteins/P37188.xml Heat-responsive suppressor hrsA P54745 HRSA_ECOLI hrsA http://ecmdb.ca/proteins/P54745.xml Glucitol/sorbitol-specific phosphotransferase enzyme IIB component P56580 PTHB_ECOLI srlE http://ecmdb.ca/proteins/P56580.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Multiphosphoryl transfer protein P69811 PTFAH_ECOLI fruB http://ecmdb.ca/proteins/P69811.xml Ascorbate-specific phosphotransferase enzyme IIA component P69820 ULAC_ECOLI ulaC http://ecmdb.ca/proteins/P69820.xml Ascorbate-specific phosphotransferase enzyme IIB component P69822 ULAB_ECOLI ulaB http://ecmdb.ca/proteins/P69822.xml Galactitol-specific phosphotransferase enzyme IIA component P69828 PTKA_ECOLI gatA http://ecmdb.ca/proteins/P69828.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Multiphosphoryl transfer protein 1 P77439 PTFX1_ECOLI fryA http://ecmdb.ca/proteins/P77439.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml PTS-dependent dihydroxyacetone kinase, dihydroxyacetone-binding subunit dhaK P76015 DHAK_ECOLI dhaK http://ecmdb.ca/proteins/P76015.xml PTS-dependent dihydroxyacetone kinase, ADP-binding subunit dhaL P76014 DHAL_ECOLI dhaL http://ecmdb.ca/proteins/P76014.xml PTS-dependent dihydroxyacetone kinase, phosphotransferase subunit dhaM P37349 DHAM_ECOLI dhaM http://ecmdb.ca/proteins/P37349.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml PTS system beta-glucoside-specific EIIBCA component P08722 PTV3B_ECOLI bglF http://ecmdb.ca/proteins/P08722.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml PTS system fructose-specific EIIBC component P20966 PTFBC_ECOLI fruA http://ecmdb.ca/proteins/P20966.xml PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml PTS system trehalose-specific EIIBC component P36672 PTTBC_ECOLI treB http://ecmdb.ca/proteins/P36672.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Glucitol/sorbitol permease IIC component P56579 PTHC_ECOLI srlA http://ecmdb.ca/proteins/P56579.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acid Phosphoenolpyruvic acid + Arbutin > Arbutin 6-phosphate + Pyruvic acid TRANS-RXN-153 Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid RXN0-2522 Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid 2.7.1.121-RXN Phosphoenolpyruvic acid + D-Mannose > Mannose 6-phosphate + Pyruvic acid TRANS-RXN-165 Phosphoenolpyruvic acid + D-Fructose > Fructose 6-phosphate + Pyruvic acid Phosphoenolpyruvic acid + N-Acetylmannosamine > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid TRANS-RXN0-446 Phosphoenolpyruvic acid + Glucosamine > Glucosamine 6-phosphate + Pyruvic acid TRANS-RXN-167A ADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acid R00200 PEPDEPHOS-RXN Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acid Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphate TRANS-RXN-169 Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid Phosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphate TRANS-RXN-168 Phosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphate Phosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate R01826 DAHPSYN-RXN Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate R03460 2.5.1.19-RXN D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <> 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate R03254 KDO-8PSYNTH-RXN Adenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + Phosphate R00199 PEPSYNTH-RXN Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid TRANS-RXN-155B 2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acid R00658 2PGADEHYDRAT-RXN Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine R00660 UDPNACETYLGLUCOSAMENOLPYRTRANS-RXN Adenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acid R00341 PEPCARBOXYKIN-RXN Carbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonate R00345 Adenosine triphosphate + Pyruvic acid + Water <> Adenosine monophosphate + Phosphoenolpyruvic acid + Phosphate R00199 PEPSYNTH-RXN Adenosine triphosphate + Pyruvic acid <> ADP + Phosphoenolpyruvic acid R00200 Phosphate + Oxalacetic acid <> Water + Phosphoenolpyruvic acid + Carbon dioxide R00345 Guanosine triphosphate + Pyruvic acid <> Guanosine diphosphate + Phosphoenolpyruvic acid R00430 dATP + Pyruvic acid <> dADP + Phosphoenolpyruvic acid R01138 dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acid R01858 Nucleoside triphosphate + Pyruvic acid <> NDP + Phosphoenolpyruvic acid R02320 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate <> Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water R03254 Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid RXN0-2522 Arbutin + Phosphoenolpyruvic acid > Arbutin 6-phosphate + Pyruvic acid TRANS-RXN-153 Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acid TRANS-RXN-157 N-Acetylmannosamine + Phosphoenolpyruvic acid > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid TRANS-RXN0-446 Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid 2.7.1.121-RXN D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid > 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate KDO-8PSYNTH-RXN Phosphate + Oxalacetic acid <> Phosphoenolpyruvic acid + Hydrogen carbonate PEPCARBOX-RXN Oxalacetic acid + Adenosine triphosphate > Carbon dioxide + Phosphoenolpyruvic acid + ADP PEPCARBOXYKIN-RXN Pyruvic acid + Adenosine triphosphate <> Hydrogen ion + ADP + Phosphoenolpyruvic acid PEPDEPHOS-RXN Water + Pyruvic acid + Adenosine triphosphate > Hydrogen ion + Phosphate + Phosphoenolpyruvic acid + Adenosine monophosphate PEPSYNTH-RXN Phosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid RXN0-17 Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acid TRANS-RXN-153A Phosphoenolpyruvic acid + Cellobiose > Cellobiose-6-phosphate + Pyruvic acid TRANS-RXN-155 Phosphoenolpyruvic acid + Chitobiose > Pyruvic acid + Diacetylchitobiose-6-phosphate TRANS-RXN-155B Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 D-fructose + Phosphoenolpyruvic acid > Fructose 1-phosphate + Pyruvic acid TRANS-RXN-158 D-fructose + Phosphoenolpyruvic acid > Fructose 6-phosphate + Pyruvic acid TRANS-RXN-158A Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 D-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acid TRANS-RXN-165 Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 Glucosamine + Phosphoenolpyruvic acid > Glucosamine 6-phosphate + Pyruvic acid TRANS-RXN-167A Phosphoenolpyruvic acid + Trehalose > Trehalose 6-phosphate + Pyruvic acid TRANS-RXN-168 Phosphoenolpyruvic acid + Sorbitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-169 Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + Phosphate UDPNACETYLGLUCOSAMENOLPYRTRANS-RXN Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate Phosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphate Inorganic phosphate + Oxalacetic acid > Water + Phosphoenolpyruvic acid + Carbonic acid Phosphoenolpyruvic acid + protein L-histidine > Pyruvic acid + protein N(pi)-phospho-L-histidine 2-Phospho-D-glyceric acid > Phosphoenolpyruvic acid + Water Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water > 3-Deoxy-D-manno-octulosonate 8-phosphate + Inorganic phosphate Adenosine triphosphate + Pyruvic acid > ADP + Phosphoenolpyruvic acid Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine > Inorganic phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine Adenosine triphosphate + Pyruvic acid + Water > Adenosine monophosphate + Phosphoenolpyruvic acid + Inorganic phosphate Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidine R02628 Phosphoenolpyruvic acid > Water + 2-Phosphoglyceric acid + 2-Phosphoglyceric acid PW_R002932 2-Phosphoglyceric acid + 2-Phosphoglyceric acid <> Water + Phosphoenolpyruvic acid PW_R003674 Phosphoenolpyruvic acid + Adenosine monophosphate + Phosphate + 2 Hydrogen ion > Adenosine triphosphate + Water + Pyruvic acid PW_R002640 Water + Adenosine triphosphate + Pyruvic acid > Adenosine monophosphate + Phosphate +2 Hydrogen ion + Phosphoenolpyruvic acid PW_R003675 Phosphoenolpyruvic acid + Adenosine diphosphate + Hydrogen ion + ADP > Adenosine triphosphate + Pyruvic acid PW_R002641 D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphate PW_R002910 shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphate PW_R002916 Oxalacetic acid + Adenosine triphosphate > Adenosine diphosphate + Carbon dioxide + Phosphoenolpyruvic acid + ADP PW_R002929 D-Arabinose 5-phosphate + Phosphoenolpyruvic acid + Water > Phosphate + 3-deoxy-D-manno-octulosonate 8-phosphate + 3-Deoxy-D-manno-octulosonate 8-phosphate PW_R003031 Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > Phosphate + UDP-N-acetyl-α-D-glucosamine-enolpyruvate PW_R003317 Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidine ADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acid D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate Adenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + Phosphate 2 2-Phospho-D-glyceric acid <> Water + Phosphoenolpyruvic acid D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate Carbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonate Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine Adenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acid ADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acid D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate 4.0 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 glucose Bioreactor, pH controlled, aerated 10.9 uM 0.0 37 oC W3110 Stationary Phase 43600 0 Park, 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 Glucose Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h 70.0 uM 6.0 37 oC BW25113 Mid-Log Phase 280000 24000 Peng, 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. 15158257 Gutnick 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 glucose Shake flask and filter culture 184.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 736000 0 Bennett, 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 Gutnick 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 glycerol Shake flask and filter culture 1340.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 5360000 0 Bennett, 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 Gutnick 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 acetate Shake flask and filter culture 909.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 3636000 0 Bennett, 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