Cyanoalanine

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132546;
ChemSpider	388802;
KEGG	C02512;
PubChem CID	439742;
UNII	B75AJA4DCJ ;
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

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]

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. Bibcode:2010JHzM..176....1G. doi:10.1016/j.jhazmat.2009.11.038. 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.

[1] 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.

[2] 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.2009.11.038. PMID 20004515.

[3] 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.

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