Cyanoalanine
From Wikipedia, the free encyclopedia
| Names | |
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| IUPAC name
(2S)-2-Amino-3-cyanopropanoic acid | |
| Other names
3-Cyano-L-alanine β-Cyanoalanine 3-Cyanoalanine, β-Cyano-L-alanine | |
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3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C4H6N2O2 | |
| Molar mass | 114.104g·mol−1 |
| Appearance | White solid |
| Melting point | 213–216°C (415–421°F; 486–489K) decomposition |
Except where otherwise noted, data are given for materials in their standard state (at 25°C [77°F], 100kPa).
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Chemical compound
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
[edit ]References
[edit ]- ↑ 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. Bibcode:2010JHzM..176....1G. doi:10.1016/j.jhazmat.2009年11月03日8. PMID 20004515.
- ↑ 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. Bibcode:2003JAChS.125..405G. doi:10.1021/ja0285262. PMID 12517152.