Cyanoalanine

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Cyanoalanine
3-Cyano-L-alanine.svg
Names
IUPAC name
(2S)-2-Amino-3-cyanopropanoic acid
Other names
3-Cyano-L-alanine
β-Cyanoalanine
3-Cyanoalanine
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
KEGG
Properties
C4H6N2O2
Molar mass 114.104 g·mol−1
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

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 asparagine enzymatically.

References[edit]

  1. ^ By Gupta, Neha; Balomajumder, Chandrajit; Agarwal, V. K. (2010). "Enzymatic mechanism and biochemistry for cyanide degradation: A review". Journal of Hazardous Materials. 176: 1–13. doi:10.1016/j.jhazmat.2009.11.038.CS1 maint: uses authors parameter (link)