O-Acetylserine

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:[1]

HO2CCH(NH2)CH2OH → HO2CCH(NH2)CH2OC(O)CH3
HO2CCH(NH2)CH2OC(O)CH3 → HO2CCH(NH2)CH2SH
O-Acetylserine
Names
IUPAC name
O-Acetyl-L-serine
Systematic IUPAC name
(2S)-3-(Acetyloxy)-2-aminopropanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
UNII
  • InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9) checkY
    Key: VZXPDPZARILFQX-UHFFFAOYSA-N checkY
  • InChI=1/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)
    Key: VZXPDPZARILFQX-UHFFFAOYAG
  • O=C(OCC(N)C(=O)O)C
Properties
C5H9NO4
Molar mass 147.13
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. Hell, R. (1997). "Molecular physiology of plant sulfur metabolism". Planta. 202 (2): 138–148. doi:10.1007/s004250050112. PMID 9202491. S2CID 2539629.
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