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Cyanoalanine

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Cyanoalanine
Names
IUPAC name (2S)-2-Amino-3-cyanopropanoic acid
Other names 3-Cyano-L-alanine
β-Cyanoalanine
3-Cyanoalanine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1
  • Key: BXRLWGXPSRYJDZ-VKHMYHEASA-N
SMILES
  • C(C#N)C(C(=O)O)N
Properties
Chemical formula C4H6N2O2
Molar mass 114.104 g·mol
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cyanoalanine (more accurately β-Cyano-L-alanine) is an amino acid with the formula NCCH2CH(NH2)CO2H. Like most amino acids, it exists as a tautomer NCCH2CH(NH3)CO2. It is a rare example of a nitrile-containing amino acid. It is a white, water-soluble solid. It can be found in common vetch seeds.

Cyanoalanine arises in nature by the action of cyanide on cysteine catalyzed by L-3-cyanoalanine synthase:

HSCH2CH(NH2)CO2H + HCN → NCCH2CH(NH2)CO2H + H2S

It is converted to aspartic acid and asparagine enzymatically.

References

  1. Gupta, Neha; Balomajumder, Chandrajit; Agarwal, V. K. (2010). "Enzymatic mechanism and biochemistry for cyanide degradation: A review". Journal of Hazardous Materials. 176 (1–3): 1–13. doi:10.1016/j.jhazmat.2009.11.038. PMID 20004515.
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