Cyanoalanine

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).^[1]

Quick facts Names, Identifiers ...

Cyanoalanine

Names
IUPAC name (2S)-2-Amino-3-cyanopropanoic acid
Other names 3-Cyano-L-alanine β-Cyanoalanine 3-Cyanoalanine, β-Cyano-L-alanine
Identifiers
CAS Number	6232-19-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:132546
ChemSpider	388802
KEGG	C02512
PubChem CID	439742
UNII	B75AJA4DCJ Y
CompTox Dashboard (EPA)	DTXSID90977873
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−1
Appearance	White solid
Melting point	213–216 °C (415–421 °F; 486–489 K) decomposition
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Cyanoalanine arises in nature by the action of cyanide on cysteine catalyzed by L-3-cyanoalanine synthase:^[2]

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.^[3]