Cyanoalanine Explained

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:^[1]

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

It is converted to aspartic acid and asparagine enzymatically.

References

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