P-Cyano-L-alanine

B Liberek. The nitrile group in peptide chemistry. V. Racemization during peptide synthesis. 4. Racemization of active esters of phthaloyl-P-cyano-L-alanine in the presence of trie thy lamine. Acad Pol Sci Ser Sci Chim 11, 677, 1963. 

P-Cyano-L-alanine and y-L-glutamyl-P-cyano-L-alanine are present in seeds of various species of Vida and Lathyrus (see Table 2), including V. sativa and V. angustifolia. The concentrations of the y-glutamyl derivative is much higher in seedlings than in seeds of V. sativa 274), and P-cyanoalanine is nearly- or totally absent from the seedlings of V. 

N -(2-Cyanoethyl)-L-glutamine was originally isolated from seeds of Lathyrus odoratus as the agent causing lathyrism in rats (299). y-L-Glutamyl-P-cyano-L-alanine was likewise isolated from seeds of Vida saliva and showed to be responsible for the toxicity of these seeds to-... 

Ressler, C., S. N. Nigam, Y. Giza, and J. Nelson Isolation and identification from common vetch of y-L-glutamyl-P-cyano-L-alanine, a bound form of the neurotoxin p-cyano-L-alanine. J. Amer. Chem. Soc. 85, 3311 (1963). 

There are many examples of nitrilase-catalyzed reactions in which amides form a considerable amount of the reaction products, such as the transformations of acrylonitrile analogs and a-fluoroarylacetonitriles by nitrilase 1 from Arabidopsis thaliana [17], the conversion of p-cyano-L-alanine into a mixture of L-asparagine and L-aspartic acid by nitrilase 4 from the same organism [18] or the transformations of mandelonitrile by nitrilase from Pseudomonas jhiorescens [19] or some fungi [8], Moreover, formamide is the only product of the cyanide transformation by cyanide hydratase. Therefore, this enzyme was classified as a lyase (EC 4.2.1.66), although it is closely related to nitrilases, as far as its aa sequence and reaction mechanism are concerned [3]. 

Piotrowski, M., Schonfelder, S., and Weiler, E.W. (2001) The Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode p-cyano-L-alanine hydratase/ nitrilase. J. Bid. Chem., 276, 2616-2621. 

With N,0 mixed donor ligands several complexes have been reported with ligands such as 4,5-dichloro-2-cyano-3,6-dione-l,4-cyclohexen-l-ol,1445 isonicotinic acid,1446 p-aminobenzoic acid,1447 alanine, histidine or histamine derivatives,1448-1450 [N(0)C(CN)2]-,1451 pyridine-carboxylate derivatives, 1452 1454 [N(pph20)2] (263),1455 bis(sulfonyl)amide derivatives,1456,1457 tris(pyridyl)-... 

Alphamethrin B p-alanine [Cyano-(3-phenoxyphenyl)-methyl] 3 (2,2-dichloroethenyl)-2,2-dimethylcyclopropane-l-carboxylate 97955-44-7... 

---