Structure via PubChem · Public domain (PubChem)
O-acetylserine
Sign in to saveAlso known as L-Serine, acetate (ester), O3-acetyl-L-serine, O-acetyl-L-serine
'''O-Acetylserine' is an α-amino acid with the chemical formula HO2CCH(NH2)CH2OC(O)CH3. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O''-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate: HO2CCH(NH2)CH2OH → HO2CCH(NH2)CH2OC(O)CH3 HO2CCH(NH2)CH2OC(O)CH3 → HO2CCH(NH2)CH2SH
Chemical data
- Formula
- C5H9NO4
- Molecular weight
- 147.13 g/mol
- IUPAC name
- (2S)-3-acetyloxy-2-azaniumylpropanoate
- SMILES
- CC(=O)OC[C@@H](C(=O)[O-])[NH3+]
- InChIKey
- VZXPDPZARILFQX-BYPYZUCNSA-N
- XLogP
- -2.8
- Polar surface area
- 94.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 147.053
Show 5 more facts
- chemical formula
- C₅H₉NO₄
- isomeric SMILES
- CC(=O)OC[C@@H](C(=O)O)N
- canonical SMILES
- CC(=O)OCC(C(=O)O)N
- found in taxon
- Homo sapiens
- subject has role
- primary metabolite
via Wikidata · CC0
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Encyclopedic overview
1 sectionsContents
- References
'''O-Acetylserine' is an α-amino acid with the chemical formula HO2CCH(NH2)CH2OC(O)CH3. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O''-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate: HO2CCH(NH2)CH2OH → HO2CCH(NH2)CH2OC(O)CH3 HO2CCH(NH2)CH2OC(O)CH3 → HO2CCH(NH2)CH2SH
==References==
Excerpted from Wikipedia’s “O-acetylserine” article, available under the CC BY-SA 4.0 licence.