Cyanoalanine is an amino acid with the formula NCCH<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. Like most amino acids, it exists as a tautomer NCCH<sub>2</sub>CH(NH<sub>3</sub><sup>+</sup>)CO<sub>2</sub><sup>âÂÂ</sup>. 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 <small>L</small>-3-cyanoalanine synthase:
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.