Chemistry:Cyanoalanine
From HandWiki
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]
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]
See also
References
- ↑ Pfeffer, Morris; Ressler, Charlotte (1967). "β-Cyanoalanine, an inhibitor of rat liver cystathionase". Biochemical Pharmacology 16 (12): 2299–2308. doi:10.1016/0006-2952(67)90217-1. PMID 6075392.
- ↑ Gupta, Neha; Balomajumder, Chandrajit; Agarwal, V. K. (2010). "Enzymatic mechanism and biochemistry for cyanide degradation: A review". Journal of Hazardous Materials 176 (1–3): 1–13. doi:10.1016/j.jhazmat.2009.11.038. PMID 20004515. Bibcode: 2010JHzM..176....1G.
- ↑ Getahun, Zelleka; Huang, Cheng-Yen; Wang, Ting; De León, Brenda; Degrado, William F.; Gai, Feng (2003). "Using Nitrile-Derivatized Amino Acids as Infrared Probes of Local Environment". Journal of the American Chemical Society 125 (2): 405–411. doi:10.1021/ja0285262. PMID 12517152. Bibcode: 2003JAChS.125..405G.
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