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MetaCyc Compound: O-acetyl-L-homoserine

Synonyms: acetylhomoserine, O-acetylhomoserine

Superclasses: an acidall carboxy acidsa carboxylatean amino acida modified amino acidan amino acid derivative
an amino acid or its derivativean amino acida modified amino acidan amino acid derivative

Summary:
Naturally occurring O-acetyl-L-homoserine was first found in the legume plant Pisum sativum in 1958 [Grobbelaar58].

Chemical Formula: C6H11NO4

Molecular Weight: 161.16 Daltons

Monoisotopic Molecular Weight: 162.0766328788 Daltons

<i>O</i>-acetyl-L-homoserine compound structure

SMILES: CC(OCCC(C([O-])=O)[N+])=O

InChI: InChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)/t5-/m0/s1

InChIKey: InChIKey=FCXZBWSIAGGPCB-YFKPBYRVSA-N

Unification Links: ChEBI:57716, KEGG:C01077, MetaboLights:MTBLC57716, PubChem:25244888

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -46.997684Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

S-methyl-5-thio-α-D-ribose 1-phosphate degradation II :
O-acetyl-L-homoserine + methanethiol → L-methionine + acetate + H+

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acidL-homotyrosine + a 2-oxo acid

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasm] + H2O[periplasm]a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-O-(β-D-galactopyranosyl)-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

L-homocysteine and L-cysteine interconversion :
O-acetyl-L-homoserine + L-cysteine ↔ L-cystathionine + acetate + H+

L-homocysteine biosynthesis :
L-homoserine + acetyl-CoA ↔ O-acetyl-L-homoserine + coenzyme A
O-acetyl-L-homoserine + hydrogen sulfide ↔ L-homocysteine + acetate + H+

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ D-erythro-sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

Enzymes inhibited by O-acetyl-L-homoserine, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: homoserine O-acetyltransferase [Yamagata87, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: O-succinylhomoserine(thiol)-lyase

Credits:
Revised 05-Dec-2013 by Caspi R, SRI International


References

Grobbelaar58: Grobbelaar, N, Steward FC (1958). "O-acetylhomoserine in Pisum." Nature 182(4646);1358-9. PMID: 13600320

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Yamagata87: Yamagata S (1987). "Partial purification and some properties of homoserine O-acetyltransferase of a methionine auxotroph of Saccharomyces cerevisiae." J Bacteriol 1987;169(8);3458-63. PMID: 3301801


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Fri Feb 12, 2016, biocyc13.