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MetaCyc Compound: O-acetyl-L-homoserine

Synonyms: acetylhomoserine, O-acetylhomoserine

Superclasses: an amino acid or its derivative an amino acid a modified amino acid an 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: 161.0688078467 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 Change Formation (ΔfG in kcal/mol): -46.997684 Inferred 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+

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+

In Reactions of unknown directionality:

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

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 SRI International Pathway Tools version 19.0 on Fri May 29, 2015, BIOCYC13A.