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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

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

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

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

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

taurine degradation IV :
taurine + 2-oxoglutarate + oxygen → 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 + H+
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:

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

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

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

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


a D-amino acid + an electron-transfer-related quinone[inner membrane] + H2O → ammonium + a 2-oxo carboxylate + an electron-transfer-related quinol[inner membrane]


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-lysophosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

Reactions known to both consume and produce the compound:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid


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- → a D-amino acid[in] + H2O[in]

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

Activator (Allosteric) of: [protein-PII] uridylyltransferase

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

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

Inhibitor (Competitive) of: α-ketoglutarate 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 [Ebner70a, Ebner70, Helmward89, Comment 2]

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


References

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

Ebner70a: 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

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 18.5 on Mon Dec 22, 2014, BIOCYC14B.