Cyanoalanine (more accurately β-Cyano-L-alanine) is an

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

with the formula NCCH₂CH(NH₂)CO₂H. Like most amino acids, it exists as a

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

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'', known as the common vetch, garden vetch, tare or simply vetch, is a nitrogen-fixing leguminous plant in the family Fabaceae. It is likely native to North Africa, Western Asia and Europe, but is now naturalized in temperate and ...

seeds. Cyanoalanine arises in nature by the action of cyanide on

cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometime ...

catalyzed by L-3-cyanoalanine synthase:{{cite journal, title=Enzymatic mechanism and biochemistry for cyanide degradation: A review, authors=By Gupta, Neha; Balomajumder, Chandrajit; Agarwal, V. K., journal=Journal of Hazardous Materials, year=2010, volume =176, issue=1–3, pages=1–13, doi=10.1016/j.jhazmat.2009.11.038, pmid=20004515 :HSCH₂CH(NH₂)CO₂H + HCN → NCCH₂CH(NH₂)CO₂H + H₂S It is converted to

aspartic acid Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. Like all other amino acids, it contains an amino group and a carboxylic acid. Its α-amino group is in the pro ...

and

asparagine Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the depro ...

enzymatically.

References

Amino acids Nitriles