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Escherichia coli K-12 substr. MG1655 Compound: glyoxylate

Synonyms: glyoxalate, glyox, glyoxylic 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

Component of:
IclR-glyox
AllR-glyox

Chemical Formula: C2HO3

Molecular Weight: 73.028 Daltons

Monoisotopic Molecular Weight: 74.0003939305 Daltons

glyoxylate compound structure

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

InChI: InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)/p-1

InChIKey: InChIKey=HHLFWLYXYJOTON-UHFFFAOYSA-M

Unification Links: CAS:298-12-4 , ChEBI:35179 , HMDB:HMDB00119 , IAF1260:33659 , KEGG:C00048 , KNApSAcK:C00001186 , MetaboLights:MTBLC36655 , PubChem:3614358

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -112

Reactions known to consume the compound:

glycolate and glyoxylate degradation I :
2 glyoxylate + H+ → CO2 + tartronate semialdehyde

glycolate and glyoxylate degradation II , glyoxylate cycle :
acetyl-CoA + glyoxylate + H2O → (S)-malate + coenzyme A + H+

Not in pathways:
glycolate + NADP+glyoxylate + NADPH + H+

Reactions known to produce the compound:

allantoin degradation to glyoxylate III :
S-ureidoglycolate → urea + glyoxylate

glycolate and glyoxylate degradation I , glycolate and glyoxylate degradation II :
glycolate + an unknown oxidized electron acceptor → glyoxylate + an unknown reduced electron acceptor

Not in pathways:
2-iminoacetate + H+ + H2O → glyoxylate + ammonium
a 5-carboxymethylaminomethyl-2-thiouridine in tRNA → a 5-aminomethyl-2-thiouridine in tRNA + glyoxylate

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:

glyoxylate cycle :
D-threo-isocitrate ↔ glyoxylate + succinate

Not in pathways:
propanoyl-CoA + glyoxylate + H2O ↔ 2-hydroxyglutarate + coenzyme A + H+

In Reactions of unknown directionality:

Not in pathways:
(4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate
IclR transcriptional repressor[membrane] + glyoxylate[membrane] = IclR-glyox[membrane]
AllR[membrane] + glyoxylate[membrane] = AllR-glyox[membrane]

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:
glyoxylate[periplasmic space]glyoxylate[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 inhibited by glyoxylate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: 2-keto-4-hydroxyglutarate aldolase [Grady81] , pyruvate dehydrogenase [Bisswanger81] , isocitrate dehydrogenase [Comment 1]

Inhibitor (Mechanism unknown) of: threonine dehydratase [Park79] , acetolactate synthase [Vinogradov05] , isocitrate dehydrogenase kinase [Nimmo84]

This compound has been characterized as an alternative substrate of the following enzymes: D-lactate dehydrogenase

In Growth Media: PMA carbon source test + glyoxylate


References

Bisswanger81: Bisswanger H (1981). "Substrate specificity of the pyruvate dehydrogenase complex from Escherichia coli." J Biol Chem 256(2);815-22. PMID: 7005225

Grady81: Grady SR, Wang JK, Dekker EE "Steady-state kinetics and inhibition studies of the aldol condensation reaction catalyzed by bovine liver and Escherichia coli 2-keto-4-hydroxyglutarate aldolase." Biochemistry 1981;20:2497-2502.

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

Nimmo86: Nimmo HG (1986). "Kinetic mechanism of Escherichia coli isocitrate dehydrogenase and its inhibition by glyoxylate and oxaloacetate." Biochem J 1986;234(2);317-23. PMID: 3521584

Park79: Park LS, Datta P (1979). "The role of glyoxylate in the regulation of biodegradative threonine dehydratase of Escherichia coli." J Biol Chem 254(16);7927-34. PMID: 381296

Vinogradov05: Vinogradov M, Kaplun A, Vyazmensky M, Engel S, Golbik R, Tittmann K, Uhlemann K, Meshalkina L, Barak Z, Hubner G, Chipman DM (2005). "Monitoring the acetohydroxy acid synthase reaction and related carboligations by circular dichroism spectroscopy." Anal Biochem 342(1);126-33. PMID: 15958189


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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 Mon Mar 30, 2015, BIOCYC13A.