Misplaced Pages

O-Acetylserine

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from O3-acetyl-L-serine)
O-Acetylserine
Names
IUPAC name O-Acetyl-L-serine
Systematic IUPAC name (2S)-3-(Acetyloxy)-2-aminopropanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)Key: VZXPDPZARILFQX-UHFFFAOYSA-N
  • InChI=1/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)Key: VZXPDPZARILFQX-UHFFFAOYAG
SMILES
  • O=C(OCC(N)C(=O)O)C
Properties
Chemical formula C5H9NO4
Molar mass 147.13
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

  1. Hell, R. (1997). "Molecular physiology of plant sulfur metabolism". Planta. 202 (2): 138–148. doi:10.1007/s004250050112. PMID 9202491. S2CID 2539629.
Encoded (proteinogenic) amino acids
General topics
Unspecified L-amino acid
By properties
Aliphatic
Aromatic
Polar, uncharged
Positive charge (pKa)
Negative charge (pKa)
Categories:
O-Acetylserine Add topic