O-Acetylserine

O-Acetylserine
Names

IUPAC name (2S)-3-Acetyloxy-2-aminopropanoic acid
Identifiers
CAS Number	5147-00-2^N 66638-22-0 (HCl)^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17981^N
ChemSpider	184^Y
DrugBank	DB01837^Y
PubChem	189
InChI InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)^Y Key: VZXPDPZARILFQX-UHFFFAOYSA-N^Y 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	183.59
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

O-Acetylserine is the 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

References

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

The encoded amino acid

General topics

By properties

Aliphatic	Branched-chain amino acids (Valine Isoleucine Leucine) Methionine Alanine Proline Glycine

Aromatic	Phenylalanine Tyrosine Tryptophan Histidine

Polar, uncharged	Asparagine Glutamine Serine Threonine

Positive charge (pK_a)	Lysine (≈10.8) Arginine (≈12.5) Histidine (≈6.1)

Negative charge (pK_a)	Aspartic acid (≈3.9) Glutamic acid (≈4.1) Cysteine (≈8.3) Tyrosine (≈10.1)

Other classifications

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