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. It can be found in common vetch seeds.
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| Names | |
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| IUPAC name
(2S)-2-Amino-3-cyanopropanoic acid
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| Other names
3-Cyano-L-alanine
β-Cyanoalanine 3-Cyanoalanine | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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 aspartic acid and asparagine enzymatically.
References edit
- ^ 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.