2.02012-05-31 10:28:08 -06002015-09-13 12:56:08 -0600ECMDB00641M2MDB000163L-GlutamineGlutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. Glutamine has a variety of biochemical functions including: 1. As any other amino acid, a major role in protein synthesis. 2. Cellular energy source, next to glucose. 3. Nitrogen donor for many anabolic processes. 4.Carbon source, refilling the Citric acid cycle. (Wikipedia)(2S)-2,5-diamino-5-oxopentanoate(2S)-2,5-diamino-5-oxopentanoic acid(2S)-2-amino-4-carbamoylbutanoate(2S)-2-amino-4-carbamoylbutanoic acid(S)-2,5-Diamino-5-oxopentanoate(S)-2,5-Diamino-5-oxopentanoic acid2-Aminoglutaramate2-Aminoglutaramic acidCebrogeng-GlutamineGamma-GlutamineGlavaminGlnGlumGluminGlutamate 5-amideGlutamate amideGlutamic acid 5-amideGlutamic acid amideGlutamineL-(+)-GlutamineL-2-AminoglutaramateL-2-Aminoglutaramic acidL-2-AminoglutaramidateL-2-Aminoglutaramidic acidL-Glutamate 5-amideL-Glutamate g-amideL-Glutamate gamma-amideL-Glutamate γ-amideL-Glutamic acid 5-amideL-Glutamic acid g-amideL-Glutamic acid gamma-amideL-Glutamic acid γ-amideL-GlutamidL-GlutamideL-GlutaminL-GlutamineL-Glutaminsaeure-5-amidLevoglutamidLevoglutamidaLevoglutamideLevoglutamidumLevoglutaminaPolyglutamineProglumideQStimulinaγ-GlutamineC5H10N2O3146.1445146.069142196(2S)-2-amino-4-carbamoylbutanoic acidL-glutamine56-85-9N[C@@H](CCC(N)=O)C(O)=OInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1ZDXPYRJPNDTMRX-VKHMYHEASA-NSolidCytosolExtra-organismPeriplasmlogp-3.32logs-0.17solubility9.78e+01 g/lmelting_point185 oClogp-4pka_strongest_acidic2.15pka_strongest_basic9.31iupac(2S)-2-amino-4-carbamoylbutanoic acidaverage_mass146.1445mono_mass146.069142196smilesN[C@@H](CCC(N)=O)C(O)=OformulaC5H10N2O3inchiInChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1inchikeyZDXPYRJPNDTMRX-VKHMYHEASA-Npolar_surface_area106.41refractivity33.11polarizability13.87rotatable_bond_count4acceptor_count4donor_count3physiological_charge0formal_charge0Alanine, aspartate and glutamate metabolismec00250Arginine and proline metabolismec00330Nitrogen metabolism
The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia.
The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere.
Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK
Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia.
Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia
Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia.
Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid.
Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia.
PW000755ec00910MetabolicPurine metabolismec00230Pyrimidine metabolismThe metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.PW000942ec00240MetabolicPhenylalanine, tyrosine and tryptophan biosynthesisec00400Amino sugar and nucleotide sugar metabolismec00520Folate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicTryptophan metabolismThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA
PW000815ec00380MetabolicAminoacyl-tRNA biosynthesisec00970Drug metabolism - other enzymesec00983Lipopolysaccharide biosynthesisE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831ec00540MetabolicGlyoxylate and dicarboxylate metabolismec00630D-Glutamine and D-glutamate metabolismL-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine.
L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter.
L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase.
D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis
UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase.
PW000769ec00471MetabolicMicrobial metabolism in diverse environmentsec01120ABC transportersec02010Two-component systemec02020Metabolic 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.
PW000886MetabolicAsparagine biosynthesisL-asparagine is synthesized in E. coli from L-aspartate by either of two reactions, utilizing either L-glutamine or ammonia as the amino group donor. Both reactions are ATP driven and yield AMP and pyrophosphate.
The first reaction is catalyzed only by asparagine synthetase B, while the second reaction is catalyzed by both asparagine synthetase A and asparagine synthetase B,
The only known role of asparagine in the metabolism of E. coli is as a constituent of protein. PW000813MetabolicAspartate metabolismAspartate (seen in the center) is synthesized from and degraded to oxaloacetate , an intermediate of the TCA cycle, by a reversible transamination reaction with glutamate. As shown here, AspC is the principal transaminase that catalyzes this reaction, but TyrB also catalyzes it. Null mutations in aspC do not confer aspartate auxotrophy; null mutations in both aspC and tyrB do.
Aspartate is a constituent of proteins and participates in several other biosyntheses as shown here( NAD biosynthesis and Beta-Alanine Metabolism . Approximately 27 percent of the cell's nitrogen flows through aspartate
Aspartate can be synthesized from fumaric acid through a aspartate ammonia lyase. Aspartate also participates in the synthesis of L-asparagine through two different methods, either through aspartate ammonia ligase or asparagine synthetase B.
Aspartate is also a precursor of fumaric acid. Again it has two possible ways of synthesizing it. First set of reactions follows an adenylo succinate synthetase that yields adenylsuccinic acid and then adenylosuccinate lyase in turns leads to fumaric acid. The second way is through argininosuccinate synthase that yields argininosuccinic acid and then argininosuccinate lyase in turns leads to fumaric acid
PW000787MetabolicL-glutamate metabolism
There are various ways by which glutamate enters the cytoplasm in E.coli. through a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter.
There are various ways by which E. coli synthesizes glutamate from L-glutamine or oxoglutaric acid.
L-glutamine, introduced into the cytoplasm by glutamine ABC transporter, can either interact with glutaminase resulting in ammonia and L-glutamic acid, or react with oxoglutaric acid, and hydrogen ion through an NADPH driven glutamate synthase resulting in L-glutamic acid.
L-glutamic acid is metabolized into L-glutamine by reacting with ammonium through a ATP driven glutamine synthase. L-glutamic acid can also be metabolized into L-aspartic acid by reacting with oxalacetic acid through an aspartate transaminase resulting in n oxoglutaric acid and L-aspartic acid. L-aspartic acid is metabolized into fumaric acid through an
aspartate ammonia-lyase. Fumaric acid can be introduced into the cytoplasm through 3 methods:
dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, and C4 dicarboxylate / orotate:H+ symporter
PW000789MetabolicL-glutamate metabolism IIPW001886MetabolicNAD biosynthesisNicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide.
Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners.
In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD.
In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD.
NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase.
As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan.
PW000829MetabolicNAD salvageEven though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+.
NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside.
Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide.
Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD.
Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD.
PW000830MetabolicSecondary Metabolites: Histidine biosynthesisHistidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.PW000984Metabolicarginine metabolismThe metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine.
L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion.
Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid.
L-arginine can be metabolized into succinic acid by two different sets of reactions:
1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and
a succinic acid. The succinic acid is then incorporated in the TCA cycle
2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cyclePW000790Metabolichistidine biosynthesisHistidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.PW000810Metabolicpeptidoglycan 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.
PW000906Metabolicpurine nucleotides de novo biosynthesisThe biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a
amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven
phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide.The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid.
Inosinic acid can be metabolized to produce dGTP and dATP three different methods each.
dGTP:
Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways:
1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP
2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP.
3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP.
dATP:
Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways:
1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP
2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP
3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP
PW000910Metabolicpurine nucleotides de novo biosynthesis 1435709748PW000960MetabolictRNA Charging 2This pathway groups together all E. coli tRNA charging reactions.PW000803MetabolictRNA chargingThis pathway groups together all E. coli tRNA charging reactions.PW000799Metaboliclipopolysaccharide biosynthesis IIE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA. A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and CMP-3-deoxy-α-D-manno-octulosonate. CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound can either interact with a phosphoethanolamine resulting in a 1,2-diacyl-sn-glycerol and a phosphoethanolamine-Kdo2-lipid A which can be exported outside the cell, or it can interact with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core. A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter. The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface.PW001905Metabolictryptophan metabolism IIThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoAPW001916MetabolicThiamin diphosphate biosynthesisPW002028Metaboliclipopolysaccharide 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.PW002062Metabolicpurine nucleotides de novo biosynthesis 2The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide(5-Phosphoribosyl-5-carboxyaminoimidazole).The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATPPW002033MetabolicO-antigen building blocks biosynthesisLipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A; the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as O-antigen.
E. coli K12 is capable of producing an O-antigen when all the rfb genes are intact. The O-antigen is part of the lipopolysaccharide and is attached to the lipid A-core component, which is separately synthesized. The O-antigen is a repeat unit composed of four sugars: glucose, N-acetylglucosamine, galactose and rhamnose.
This pathway depicts the synthesis of three of these sugars. UDP-galactose is transformed from its pyranose form to its furanose form. dTTP glucose-1-phosphate is derivatized to dTDP-rhamnose. Fructose-6-phosphate gains an amino group, incorporates an acetate moiety and then acquires a nucleoside diphosphate resulting in UDP-N-acetyl-D-glucosamine.(EcoCyc)PW002089Metabolicasparagine biosynthesis IASPARAGINE-BIOSYNTHESISNAD salvage pathway IPYRIDNUCSAL-PWYtRNA chargingTRNA-CHARGING-PWYNAD biosynthesis I (from aspartate)PYRIDNUCSYN-PWYarginine biosynthesis IARGSYN-PWYguanosine nucleotides <i>de novo</i> biosynthesisPWY-6125glutamine degradation IGLUTAMINDEG-PWYglutamine biosynthesis IGLNSYN-PWYNitrogen Regulation Two-Component SystemNRI-PWYpyrimidine ribonucleotides interconversionPWY-5687-1superpathway of 5-aminoimidazole ribonucleotide biosynthesisPWY-62775-aminoimidazole ribonucleotide biosynthesis IPWY-61215-aminoimidazole ribonucleotide biosynthesis IIPWY-6122UDP-<i>N</i>-acetyl-D-glucosamine biosynthesis IUDPNAGSYN-PWYuridine-5'-phosphate biosynthesisPWY-5686glutamate biosynthesis IGLUTSYN-PWYhistidine biosynthesisHISTSYN-PWY<i>p</i>-aminobenzoate biosynthesisPWY-6543tryptophan biosynthesisTRPSYN-PWYSpecdb::CMs585Specdb::CMs586Specdb::CMs587Specdb::CMs1168Specdb::CMs1398Specdb::CMs1441Specdb::CMs1722Specdb::CMs2386Specdb::CMs30202Specdb::CMs30308Specdb::CMs30738Specdb::CMs30791Specdb::CMs31181Specdb::CMs31182Specdb::CMs31183Specdb::CMs31184Specdb::CMs32288Specdb::CMs32289Specdb::CMs32290Specdb::CMs32291Specdb::CMs32292Specdb::CMs37669Specdb::CMs135670Specdb::CMs143404Specdb::CMs1071123Specdb::EiMs1084Specdb::NmrOneD1244Specdb::NmrOneD1452Specdb::NmrOneD2473Specdb::NmrOneD3166Specdb::NmrOneD144630Specdb::NmrOneD144631Specdb::NmrOneD144632Specdb::NmrOneD144633Specdb::NmrOneD144634Specdb::NmrOneD144635Specdb::NmrOneD144636Specdb::NmrOneD144637Specdb::NmrOneD144638Specdb::NmrOneD144639Specdb::NmrOneD144640Specdb::NmrOneD144641Specdb::NmrOneD144642Specdb::NmrOneD144643Specdb::NmrOneD144644Specdb::NmrOneD144645Specdb::NmrOneD144646Specdb::NmrOneD144647Specdb::NmrOneD144648Specdb::NmrOneD144649Specdb::NmrOneD166479Specdb::MsMs879Specdb::MsMs880Specdb::MsMs881Specdb::MsMs4283Specdb::MsMs4284Specdb::MsMs4285Specdb::MsMs4286Specdb::MsMs4287Specdb::MsMs4288Specdb::MsMs4289Specdb::MsMs4290Specdb::MsMs4291Specdb::MsMs4292Specdb::MsMs4293Specdb::MsMs4294Specdb::MsMs4295Specdb::MsMs4296Specdb::MsMs4297Specdb::MsMs4298Specdb::MsMs4299Specdb::MsMs4300Specdb::MsMs4301Specdb::MsMs4302Specdb::MsMs4303Specdb::MsMs4304Specdb::NmrTwoD1397Specdb::NmrTwoD2096HMDB0064159615746C0006418050GLNGLN_LFZWL-GlutamineKeseler, I. 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Ann Surg. 1998 Feb;227(2):302-8.9488531Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6.10483898Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74.11408280Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan. Synthesis of L-glutamine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.http://hmdb.ca/system/metabolites/msds/000/000/560/original/HMDB00641.pdf?1358894675L-asparaginase 2P00805ASPG2_ECOLIansBhttp://ecmdb.ca/proteins/P00805.xmlAnthranilate synthase component 1P00895TRPE_ECOLItrpEhttp://ecmdb.ca/proteins/P00895.xmlPara-aminobenzoate synthase glutamine amidotransferase component IIP00903PABA_ECOLIpabAhttp://ecmdb.ca/proteins/P00903.xmlAnthranilate synthase component IIP00904TRPG_ECOLItrpDhttp://ecmdb.ca/proteins/P00904.xmlGlutaminyl-tRNA synthetaseP00962SYQ_ECOLIglnShttp://ecmdb.ca/proteins/P00962.xmlCarbamoyl-phosphate synthase large chainP00968CARB_ECOLIcarBhttp://ecmdb.ca/proteins/P00968.xmlGMP synthase [glutamine-hydrolyzing]P04079GUAA_ECOLIguaAhttp://ecmdb.ca/proteins/P04079.xmlPara-aminobenzoate synthase component 1P05041PABB_ECOLIpabBhttp://ecmdb.ca/proteins/P05041.xmlGlutamate synthase [NADPH] large chainP09831GLTB_ECOLIgltBhttp://ecmdb.ca/proteins/P09831.xmlGlutamate synthase [NADPH] small chainP09832GLTD_ECOLIgltDhttp://ecmdb.ca/proteins/P09832.xmlCarbamoyl-phosphate synthase small chainP0A6F1CARA_ECOLIcarAhttp://ecmdb.ca/proteins/P0A6F1.xmlGlutaminase 2P0A6W0GLSA2_ECOLIglsA2http://ecmdb.ca/proteins/P0A6W0.xmlCTP synthaseP0A7E5PYRG_ECOLIpyrGhttp://ecmdb.ca/proteins/P0A7E5.xmlGlutamine synthetaseP0A9C5GLNA_ECOLIglnAhttp://ecmdb.ca/proteins/P0A9C5.xmlAmidophosphoribosyltransferaseP0AG16PUR1_ECOLIpurFhttp://ecmdb.ca/proteins/P0AG16.xmlPhosphoribosylformylglycinamidine synthaseP15254PUR4_ECOLIpurLhttp://ecmdb.ca/proteins/P15254.xmlGlucosamine--fructose-6-phosphate aminotransferase [isomerizing]P17169GLMS_ECOLIglmShttp://ecmdb.ca/proteins/P17169.xmlNH(3)-dependent NAD(+) synthetaseP18843NADE_ECOLInadEhttp://ecmdb.ca/proteins/P18843.xmlAsparagine synthetase B [glutamine-hydrolyzing]P22106ASNB_ECOLIasnBhttp://ecmdb.ca/proteins/P22106.xmlGlutaminase 1P77454GLSA1_ECOLIglsA1http://ecmdb.ca/proteins/P77454.xmlGamma-glutamylputrescine synthetaseP78061PUUA_ECOLIpuuAhttp://ecmdb.ca/proteins/P78061.xmlGlutamine transport system permease protein glnPP0AEQ6GLNP_ECOLIglnPhttp://ecmdb.ca/proteins/P0AEQ6.xmlGlutamine transport ATP-binding protein glnQP10346GLNQ_ECOLIglnQhttp://ecmdb.ca/proteins/P10346.xmlImidazole glycerol phosphate synthase subunit hisHP60595HIS5_ECOLIhisHhttp://ecmdb.ca/proteins/P60595.xmlImidazole glycerol phosphate synthase subunit hisFP60664HIS6_ECOLIhisFhttp://ecmdb.ca/proteins/P60664.xmlGlutamine-binding periplasmic proteinP0AEQ3GLNH_ECOLIglnHhttp://ecmdb.ca/proteins/P0AEQ3.xmlUncharacterized amino-acid ABC transporter ATP-binding protein yecCP37774YECC_ECOLIyecChttp://ecmdb.ca/proteins/P37774.xmlInner membrane amino-acid ABC transporter permease protein yecSP0AFT2YECS_ECOLIyecShttp://ecmdb.ca/proteins/P0AFT2.xmlGlutamine transport system permease protein glnPP0AEQ6GLNP_ECOLIglnPhttp://ecmdb.ca/proteins/P0AEQ6.xmlGlutamine transport ATP-binding protein glnQP10346GLNQ_ECOLIglnQhttp://ecmdb.ca/proteins/P10346.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlGlutamine-binding periplasmic proteinP0AEQ3GLNH_ECOLIglnHhttp://ecmdb.ca/proteins/P0AEQ3.xml2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + PhosphateR00575CARBPSYN-RXNAdenosine triphosphate + Water + L-Glutamine > ADP + L-Glutamine + Hydrogen ion + PhosphateABC-12-RXNAdenosine triphosphate + Water + L-Glutamine > ADP + L-Glutamine + Hydrogen ion + PhosphateABC-12-RXNChorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidR00986ANTHRANSYN-RXNL-Glutamine + Water > L-Glutamate + AmmoniumL-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ionalpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPR00114Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-GlutamateR01716PABASYN-RXNAdenosine triphosphate + L-Glutamate + Ammonium > ADP + L-Glutamine + Hydrogen ion + PhosphateL-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + PyrophosphateR00578ASNSYNB-RXNAdenosine triphosphate + L-Glutamine + tRNA(Gln) > Adenosine monophosphate + L-Glutaminyl-tRNA(Gln) + PyrophosphateL-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate + 5-PhosphoribosylamineR01072PRPPAMIDOTRANS-RXNAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + PyrophosphateR01231GMP-SYN-GLUT-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateR04463FGAMSYN-RXNAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateR00573CTPSYN-RXNFructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-GlutamateR00768L-GLN-FRUCT-6-P-AMINOTRANS-RXN2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ionR000932 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ionR00114Adenosine triphosphate + L-Glutamate + Ammonia <> ADP + Phosphate + L-GlutamineR00253GLUTAMINESYN-RXNL-Glutamine + Water <> L-Glutamate + AmmoniaR00256GLUTAMIN-RXNAdenosine triphosphate + Uridine triphosphate + L-Glutamine + Water <> ADP + Phosphate + Cytidine triphosphate + L-GlutamateR005732 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water <>2 ADP + Phosphate + L-Glutamate + CarbamoylphosphateR00575Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-GlutamateR00578Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR009865-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + WaterR01072Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-GlutamateR01231Adenosine triphosphate + L-Glutamine + tRNA(Gln) + tRNA(Gln) <> Adenosine monophosphate + Pyrophosphate + Glutaminyl-tRNA + Glutaminyl-tRNAR03652Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateR04463FGAMSYN-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-GlutamateR04558GLUTAMIDOTRANS-RXN6-Thioxanthine 5'-monophosphate + Adenosine triphosphate + L-Glutamine + Water <> 6-Thioguanosine monophosphate + Adenosine monophosphate + Pyrophosphate + L-GlutamateR08244Adenosine triphosphate + L-Glutamine + Water > ADP + Phosphate + L-Glutamine + Hydrogen ionABC-12-RXNAdenosine triphosphate + L-Glutamine + Water > ADP + Phosphate + L-Glutamine + Hydrogen ionABC-12-RXNChorismate + L-Glutamine > Hydrogen ion + 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateR00986ANTHRANSYN-RXNAdenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water > Hydrogen ion + Carbamoylphosphate + L-Glutamate + Phosphate + ADPCARBPSYN-RXNAdenosine triphosphate + Uridine triphosphate + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Cytidine triphosphate + L-GlutamateCTPSYN-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateFGAMSYN-RXNL-Glutamate + NADP < Hydrogen ion + L-Glutamine + Oxoglutaric acid + NADPHGLUTAMATESYN-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICARGLUTAMIDOTRANS-RXNL-Glutamine + Water > Hydrogen ion + L-Glutamate + AmmoniaGLUTAMIN-RXNAmmonia + L-Glutamate + Adenosine triphosphate > L-Glutamine + ADP + PhosphateGLUTAMINESYN-RXNWater + L-Glutamine + Xanthylic acid + Adenosine triphosphate > Hydrogen ion + L-Glutamate + Guanosine monophosphate + Pyrophosphate + Adenosine monophosphateR01231GMP-SYN-GLUT-RXNFructose 6-phosphate + L-Glutamine > Glucosamine 6-phosphate + L-GlutamateL-GLN-FRUCT-6-P-AMINOTRANS-RXNAdenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD + L-GlutamateNAD-SYNTH-GLN-RXN5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + WaterR01072PRPPAMIDOTRANS-RXNala-gln + Water > L-Alanine + L-GlutamineRXN0-6976gly-gln + Water > Glycine + L-GlutamineRXN0-6983Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate2 Adenosine triphosphate + L-Glutamine + Carbonic acid + Water >2 ADP + Inorganic phosphate + L-Glutamate + CarbamoylphosphateL-Glutamine + Fructose 6-phosphate > L-Glutamate + D-glucosamine 6-phosphateAdenosine triphosphate + L-Glutamate + Ammonia > ADP + Inorganic phosphate + L-GlutamineL-Glutamine + Water > L-Glutamate + AmmoniaR00256GLUTAMIN-RXN2 L-Glutamate + NADP > L-Glutamine + Oxoglutaric acid + NADPHGLUTAMATESYN-RXNAdenosine triphosphate + Xanthylic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-Glutamine > imidazole-glycerol phosphate + N5-Carboxyaminoimidazole ribonucleotide + L-Glutamate + WaterChorismate + L-Glutamine > 4-Amino-4-deoxychorismate + L-Glutamate5-Phosphoribosylamine + Pyrophosphate + L-Glutamate > L-Glutamine + Phosphoribosyl pyrophosphate + WaterAdenosine triphosphate + 5'-phosphoribosyl-N-formylglycinamide + L-Glutamine + Water > ADP + Inorganic phosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine + L-GlutamateChorismate + L-Glutamine > 2-Aminobenzoic acid + Pyruvic acid + L-GlutamateAdenosine triphosphate + Uridine triphosphate + L-Glutamine + Water + Ammonia <> ADP + Phosphate + Cytidine triphosphate + L-GlutamateR00573 2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + CarbamoylphosphateR00575 2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ionR00114 Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-GlutamateR00578 Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-GlutamateR01231 Ammonia + L-Glutamic acid + Adenosine triphosphate + Oxoglutaric acid + L-Glutamate <> Phosphate + L-Glutamine + Adenosine diphosphate + ADPPW_R002433L-Glutamic acid + Adenosine triphosphate + Ammonium + L-Glutamate > L-Glutamine + Hydrogen ion + Adenosine diphosphate + Phosphate + ADPPW_R0026652 L-Glutamic acid + NADP + 2 L-Glutamate > L-Glutamine + NADPH + Hydrogen ion + Oxoglutaric acid + NADPHPW_R002435L-Glutamine + Oxoglutaric acid + NADPH + Hydrogen ion + NADPH >2 L-Glutamic acid + NADP +2 L-GlutamatePW_R002669L-Glutamine + Water > L-Glutamic acid + Ammonia + L-GlutamatePW_R002514Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + L-Asparagine + L-GlutamatePW_R002643Hydrogen carbonate + Water + L-Glutamine + 2 Adenosine triphosphate >2 Adenosine diphosphate + Phosphate + L-Glutamic acid +2 Hydrogen ion + Carbamoylphosphate +2 ADP + L-GlutamatePW_R002677L-Glutamine + Adenosine triphosphate + Hydrogen ion + tRNA(Gln) > Adenosine diphosphate + Pyrophosphate + L-Glutaminyl-tRNA(Gln) + ADPPW_R002833Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-GlutamatePW_R002869L-Aspartic acid + Water + Adenosine triphosphate + L-Glutamine + L-Aspartic acid > L-Asparagine + Hydrogen ion + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate + L-Asparagine + L-GlutamatePW_R002887Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-GlutamatePW_R002894Nicotinic acid adenine dinucleotide + Water + L-Glutamine + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + NAD + L-GlutamatePW_R003011D-tagatofuranose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamic acid + L-GlutamatePW_R003307Fructose 6-phosphate + L-Glutamine + Fructose 6-phosphate > L-Glutamic acid + Glucosamine 6-phosphate + L-GlutamatePW_R003565Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismatePW_R003403Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-GlutamatePW_R0034105'-Phosphoribosyl-N-formylglycinamide + Water + L-Glutamine + Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide > 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + L-Glutamic acid + Phosphate + Adenosine diphosphate + Hydrogen ion + L-Glutamate + ADPPW_R003413Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-GlutamatePW_R003427Uridine triphosphate + L-Glutamine + Water + Adenosine triphosphate + Uridine triphosphate > Adenosine diphosphate + Hydrogen ion + Phosphate + L-Glutamic acid + Cytidine triphosphate + ADP + L-GlutamatePW_R003533L-Glutamine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Glutamine + ADPPW_RCT000107L-Glutamine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Glutamine + ADPPW_RCT000107D-tagatofuranose 6-phosphate + L-Glutamine <> D-glucosamine 6-phosphate + L-GlutamatePW_R006103Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-GlutamateL-Glutamine + Water <> L-Glutamate + AmmoniaAdenosine triphosphate + L-Glutamine + tRNA(Gln) <> Adenosine monophosphate + Pyrophosphate + Glutaminyl-tRNAL-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine5 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + WaterAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphatealpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPAdenosine triphosphate + L-Glutamate + Ammonia <> ADP + Phosphate + L-GlutamineFructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-GlutamateChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidChorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acidL-Glutamine + Water <> L-Glutamate + AmmoniaChorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-GlutamateAdenosine triphosphate + L-Glutamine + tRNA(Gln) <> Adenosine monophosphate + Pyrophosphate + Glutaminyl-tRNAL-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-PhosphoribosylamineAdenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateAdenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphate2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ionalpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADPFructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-GlutamateGutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture3810.0uM0.037 oCK12 NCM3722Mid-Log Phase152400000Bennett, 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 culture4950.0uM0.037 oCK12 NCM3722Mid-Log Phase198000000Bennett, 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 culture3060.0uM0.037 oCK12 NCM3722Mid-Log Phase122400000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.1956162148 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h494.0uM0.037 oCBW25113Stationary Phase, glucose limited19760000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776Luria-Bertani (LB) mediaShake flask184.0uMtrue23.037 oCBL21 DE3Stationary phase cultures (overnight culture)73560092000Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911Luria-Bertani (LB) mediaShake flask248.67uMtrue19.8637 oCBL21 DE3Stationary phase cultures (overnight culture)99466779431Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911