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Escherichia coli K-12 substr. MG1655 Compound: 2-oxoglutarate

Synonyms: 2-oxoglutarate, ketoglutarate, α-ketoglutarate, 2-oxoglutaric acid, α-ketoglutaric acid, α-oxoglutarate, 2-ketoglutaric acid, 2-ketoglutarate, 2-oxopentanedionic acid, 2-oxopentanedionate, a-ketoglutaric acid

Superclasses: an acid all carboxy acids a carboxylate a 2-oxo acid a 2-oxo carboxylate
an acid all carboxy acids a carboxylate a 2-oxo carboxylate

Chemical Formula: C5H4O5

Molecular Weight: 144.08 Daltons

Monoisotopic Molecular Weight: 146.0215233031 Daltons

2-oxoglutarate compound structure

SMILES: C(CC([O-])=O)C(=O)C([O-])=O

InChI: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2

InChIKey: InChIKey=KPGXRSRHYNQIFN-UHFFFAOYSA-L

Unification Links: CAS:328-50-7 , ChEBI:16810 , ChemSpider:144236 , HMDB:HMDB00208 , IAF1260:33565 , KEGG:C00026 , KNApSAcK:C00000769 , MetaboLights:MTBLC16810 , PubChem:164533

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -189.6

Reactions known to consume the compound:

1,4-dihydroxy-2-naphthoate biosynthesis I :
isochorismate + 2-oxoglutarate + H+ → 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2

2-oxoglutarate decarboxylation to succinyl-CoA :
2-oxoglutarate + a [2-oxoglutarate dehydrogenase E2 protein] N6-lipoyl-L-lysine + H+ → a [2-oxoglutarate dehydrogenase E2 protein] N6-S-succinyldihydrolipoyl-L-lysine + CO2

hydrogen sulfide biosynthesis I :
2-oxoglutarate + L-cysteine → L-glutamate + 3-mercaptopyruvate

L-glutamate biosynthesis I :
2 L-glutamate + NADP+ ← L-glutamine + 2-oxoglutarate + NADPH + H+

putrescine degradation I :
putrescine + 2-oxoglutarate → 4-aminobutanal + L-glutamate

taurine degradation IV :
taurine + 2-oxoglutarate + oxygen → 2-aminoacetaldehyde + sulfite + succinate + CO2 + H+

TCA cycle I (prokaryotic) :
2-oxoglutarate + coenzyme A + NAD+ → succinyl-CoA + CO2 + NADH

Not in pathways:
a [50S ribosomal subunit protein L16]-L-arginine81 + 2-oxoglutarate + oxygen → a [50S ribosomal subunit protein L16]-(3R)-3-hydroxy-L-arginine81 + succinate + CO2
a methylated nucleobase within DNA + 2-oxoglutarate + oxygen → a nucleobase within DNA + CO2 + formaldehyde + succinate
N3-methylcytosine + 2-oxoglutarate + oxygen → cytosine + CO2 + formaldehyde + succinate + H+
1-ethyladenine + 2-oxoglutarate + oxygen → adenine + CO2 + acetaldehyde + succinate
N1-methyladenine + 2-oxoglutarate + oxygen → adenine + CO2 + formaldehyde + succinate

Reactions known to produce the compound:

L-histidine biosynthesis :
imidazole acetol-phosphate + L-glutamate → L-histidinol-phosphate + 2-oxoglutarate

L-ornithine biosynthesis :
N-acetyl-L-ornithine + 2-oxoglutarateN-acetyl-L-glutamate 5-semialdehyde + L-glutamate

mixed acid fermentation , TCA cycle I (prokaryotic) :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH

Not in pathways:
(S)-2-hydroxyglutarate + oxygen → 2-oxoglutarate + hydrogen peroxide

Not in pathways:
a D-amino acid + an electron-transfer quinone[inner membrane] + H2O → ammonium + a 2-oxo carboxylate + an electron-transfer quinol[inner membrane]

Not in pathways:
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-acyl 2-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

Reactions known to both consume and produce the compound:

4-aminobutanoate degradation I , 4-aminobutanoate degradation II :
2-oxoglutarate + 4-aminobutanoate ↔ L-glutamate + succinate semialdehyde

dTDP-N-acetylthomosamine biosynthesis :
dTDP-thomosamine + 2-oxoglutarate ↔ dTDP-4-dehydro-6-deoxy-α-D-glucopyranose + L-glutamate

L-alanine biosynthesis I , L-valine biosynthesis :
L-valine + 2-oxoglutarate ↔ 3-methyl-2-oxobutanoate + L-glutamate

L-alanine biosynthesis II :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

L-arginine degradation II (AST pathway) :
N2-succinyl-L-ornithine + 2-oxoglutarate ↔ N2-succinyl-L-glutamate 5-semialdehyde + L-glutamate

L-aspartate biosynthesis , L-glutamate degradation II :
L-aspartate + 2-oxoglutarate ↔ oxaloacetate + L-glutamate

L-glutamate biosynthesis III :
L-glutamate + NADP+ + H2O ↔ ammonium + 2-oxoglutarate + NADPH + H+

L-isoleucine biosynthesis I (from threonine) :
L-isoleucine + 2-oxoglutarate ↔ (S)-3-methyl-2-oxopentanoate + L-glutamate

L-leucine biosynthesis :
L-leucine + 2-oxoglutarate ↔ 4-methyl-2-oxopentanoate + L-glutamate

L-lysine biosynthesis I :
2-oxoglutarate + N-succinyl-L,L-2,6-diaminopimelate ↔ L-glutamate + N-succinyl-2-amino-6-ketopimelate

L-phenylalanine biosynthesis I :
2-oxo-3-phenylpropanoate + L-glutamate ↔ L-phenylalanine + 2-oxoglutarate

L-serine biosynthesis :
3-phospho-L-serine + 2-oxoglutarate ↔ 3-phospho-hydroxypyruvate + L-glutamate

L-tyrosine biosynthesis I :
L-tyrosine + 2-oxoglutarate ↔ 4-hydroxyphenylpyruvate + L-glutamate

polymyxin resistance :
UDP-4-amino-4-deoxy-β-L-arabinopyranose + 2-oxoglutarate ↔ UDP-β-L-threo-pentapyranos-4-ulose + L-glutamate

pyridoxal 5'-phosphate biosynthesis I :
2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate ↔ 4-phospho-hydroxy-L-threonine + 2-oxoglutarate

Not in pathways:
(R)-2-hydroxyglutarate + NAD+2-oxoglutarate + NADH + H+
putrescine + 2-oxoglutarate ↔ L-glutamate + 1-pyrroline + H2O
L-kynurenine + 2-oxoglutarate ↔ L-glutamate + 4-(2-aminophenyl)-2,4-dioxobutanoate
an aromatic amino acid + 2-oxoglutarate ↔ an aromatic oxo-acid + L-glutamate
an aliphatic α,ω-diamine + 2-oxoglutarate ↔ an aliphatic ω-aminoaldehyde + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
2-hydroxyglutarate + NAD+ = 2-oxoglutarate + NADH + H+
oxalosuccinate + H+ = 2-oxoglutarate + CO2
(S)-2-hydroxyglutarate + NAD+ = 2-oxoglutarate + NADH + H+
2-oxoglutarate + SucB-lipoate = SucB-S-succinyldihydrolipoate + CO2

Not in pathways:
L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid

Not in pathways:
a 2-acyl 1-lyso-phosphatidylcholine + H2O = a carboxylate + sn-glycero-3-phosphocholine + H+
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]

In Transport reactions:
2-oxoglutarate[periplasmic space] + H+[periplasmic space]2-oxoglutarate[cytosol] + H+[cytosol]

In Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e-[membrane] → a D-amino acid[in] + H2O[in]

Enzymes activated by 2-oxoglutarate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: fructose bisphosphate aldolase [Baldwin78] , glutamine synthetase deadenylase [Shapiro69, Shapiro68] , isocitrate dehydrogenase phosphatase [Nimmo84]

Enzymes inhibited by 2-oxoglutarate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: (S)-2-hydroxyglutarate reductase [Zhao96, Comment 1] , (R)-2-hydroxyglutarate reductase [Zhao96, Comment 1] , citrate synthase

Inhibitor (Mechanism unknown) of: phosphoenolpyruvate synthetase [Chulavatnatol73] , isocitrate lyase , isocitrate dehydrogenase kinase [Nimmo84] , N-succinyldiaminopimelate aminotransferase [Peterkofsky61] , glutamine synthetase adenylyltransferase [Ebner70, Ebner70a, Helmward89, Comment 2]

In Growth Media: PMA carbon source test + 2-oxoglutarate


References

Baldwin78: Baldwin SA, Perham RN (1978). "Novel kinetic and structural properties of the class-I D-fructose 1,6-bisphosphate aldolase from Escherichia coli (Crookes' strain)." Biochem J 1978;169(3);643-52. PMID: 348198

Chulavatnatol73: Chulavatnatol M, Atkinson DE (1973). "Phosphoenolpyruvate synthetase from Escherichia coli. Effects of adenylate energy charge and modifier concentrations." J Biol Chem 248(8);2712-5. PMID: 4572511

Ebner70: Ebner E, Wolf D, Gancedo C, Elsasser S, Holzer H (1970). "ATP: glutamine synthetase adenylyltransferase from Escherichia coli B. Purification and properties." Eur J Biochem 1970;14(3);535-44. PMID: 4920894

Ebner70a: Ebner E, Gancedo C, Holzer H "ATP:Glutamine synthetase adenylyltransferase (Escherichia coli B)." Methods in Enzymology 1970; 17A:922-927.

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Nimmo84: Nimmo GA, Nimmo HG (1984). "The regulatory properties of isocitrate dehydrogenase kinase and isocitrate dehydrogenase phosphatase from Escherichia coli ML308 and the roles of these activities in the control of isocitrate dehydrogenase." Eur J Biochem 1984;141(2);409-14. PMID: 6329757

Peterkofsky61: Peterkofsky B, Gilvarg C (1961). "N-Succinyl-L-diaminopimelic-glutamic transaminase." J Biol Chem 236;1432-8. PMID: 13734750

Shapiro68: Shapiro BM, Stadtman ER (1968). "Glutamine synthetase deadenylylating enzyme." Biochem Biophys Res Commun 1968;30(1);32-7. PMID: 4866293

Shapiro69: Shapiro BM (1969). "The glutamine synthetase deadenylylating enzyme system from Escherichia coli. Resolution into two components, specific nucleotide stimulation, and cofactor requirements." Biochemistry 8(2);659-70. PMID: 4893578

Zhao96: Zhao G, Winkler ME (1996). "A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria." J Bacteriol 1996;178(1);232-9. PMID: 8550422


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Wed Sep 2, 2015, biocyc13.