Cyanoalanine 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 (Vicia sativa).
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.
When cyanoalanine is introduced into proteins, it's CN vibration serves as a reporter of the local environment.
See also β-Ethynylserine Propargylglycine
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