3-cyano-L-alanine

Names

[ Name ]:
3-cyano-L-alanine

[Synonym ]:
AmbotzHAA5740
3-cyano-L-alanine
b-Cyano-L-Alanine
Propanoic acid, 2-amino-3-cyano-, (2S)-
(2S)-2-Amino-3-cyanopropanoic acid
L-3-Cyanoalanine
β-Cyano-L-alanine
(S)-2-amino-3-cyanopropanoic acid
L-Alanine,3-cyano

Biological Activity

[Description]:

β-cyano-L-Alanine (Beta-cyano-l-alanine), a nitrile of widespread occurrence in higher plants, is enzymatically produced by cyanoalanine synthase from cyanide and cysteine as substrates[1]. β-cyano-L-Alanine abolishes the protective effect of ethanol on cerebral ischemia/reperfusion (I/R) injury[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vivo]

β-cyano-L-Alanine (intraperitoneally; 50 mg/kg) abolishes the protective effect of ethanol on cerebral ischemia/reperfusion (I/R) injury. Animal Model: Adult (postnatal age: 60 days) male C57BL/6J mice (25-30 g) gavage-fed with ethanol[2] Dosage: 50 mg/kg Administration: Intraperitoneally Result: Abolished the protective effect of ethanol on cerebral I/R injury.

[References]

[1]. Piotrowski M, et al. The Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode beta-cyano-L-alanine hydratase/nitrilase.J Med Chem. J Biol Chem. 2001 Jan 26;276(4):2616-21.

[2]. McCarter KD, et al. Influence of low-dose alcohol consumption on post-ischemic inflammation: Role of cystathionine γ-lyase. Alcohol. 2019 May;76:81-89.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
368.1±32.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄H₆N₂O₂

[ Molecular Weight ]:
114.103

[ Flash Point ]:
176.4±25.1 °C

[ Exact Mass ]:
114.042931

[ PSA ]:
87.11000

[ LogP ]:
-0.72

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.502

[ Storage condition ]:
-20°C

MSDS

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Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2926909090

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2926909090

[ Summary ]:
HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism.

Proc. Natl. Acad. Sci. U. S. A. 104(47) , 18848-53, (2007)

Members of the nitrilase 4 (NIT4) family of higher plants catalyze the conversion of beta-cyanoalanine to aspartic acid and asparagine, a key step in cyanide detoxification. Grasses (Poaceae) possess ...

Vicianin, prunasin, and beta-cyanoalanine in common vetch seed as sources of urinary thiocyanate in the rat.

J. Agric. Food Chem. 49(10) , 5075-80, (2001)

When young rats were fed a diet containing common vetch seed for 1 month, they excreted in the urine approximately 7 times more thiocyanate than they had ingested. Vicianin, prunasin, and beta-cyanoal...

Maize nitrilases have a dual role in auxin homeostasis and beta-cyanoalanine hydrolysis.

J. Exp. Bot. 58(15-16) , 4225-33, (2007)

The auxin indole-3-acetic acid (IAA), which is essential for plant growth and development, is suggested to be synthesized via several redundant pathways. In maize (Zea mays), the nitrilase ZmNIT2 is e...