3-cyano-L-alanine

FIGURE 8.8 H2S production in vascular tissues. IPS production by aorta homogenate (upper panel), cultured rat vascular smooth muscle cells (VSMCs middle panel), and intact rat aorta occurs after the addition of substrate L-cysteine (L-cys) and cofactor pyridoxal L-phosphate (PLP) for the enzyme CGL located in vascular tissue. H2S production is inhibited after the CGL. 3 cyano-L-alanine (BCA) is added. Ferric Lucina pectinata hemoglobin I (metHb) is added to confirm H2S production. The quantity of metHb-sulfide produced, determined spectrophotometrically, matched the levels of H2S detected by the PHSS (after [41]). 

Piotrowski, M., Schonfelder, S., and Weiler, W.E. 2001. The Th Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode 3-cyano-l-alanine hydratase/nitrilase. Journal of Biological Chemistry, 276 2616-21. 

Ressler, C. (1962) Isolation and identification from common vetch of the neurotoxin (3-cyano-L-alanine, a possible factor in neurolathyrism. J. Biol. Chem. 237, 733-735. 

Several enzymes which perform reactions at the a-carbon of amino acids are also known to catalyze an apparently unrelated exchange of the j8-hydrogens of their substrates. This capability renders glutamic-pyruvic transaminase (alanine aminotransferase) susceptible to inhibition by propargylglycine (Marcotte and Walsh, 1975), presumably by the mechanism described above. Alanine transaminase is inactivated by /3-cyano-L-alanine in an analogous manner, although... 

Amino Acids from 3-Cyano-L-alanine and Asparagine Nonprotein Amino Acids Developed from Glutamic Acid Other Nonprotein Amino Acids Sulfur-Containing Amino Acids Djenkolic Acid L-Indospicine Albiziine... 

AMINO ACIDS FROM 3-CYANO-l-ALANINE AND ASPARAGINE... 

III 3-Cyano-L-alanine common vetch Vida saliva Fabaceae... 

A soln. of dicyclohexylcarbodiimide in pyridine added portionwise with stirring at 16-20° during 30 min. to a soln. of carbobenzoxy-L-asparagine in pyridine, and the product isolated after not longer than 3 hrs. at this temp. carbo-benzoxy-j -cyano-L-alanine. Y 78%. F. e. s. C. Kessler and H. Ratzkin, J. Org. Ghem. 26, 3356 (1961). 

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]. 

Dicyclohexylammonium /9-cyano-N-o-nitrophenylsulfenyl-L-alaninate treated with a soln. of thioacetamide in 1 3 acetic acid-methanol, and the product isolated after 5 min. ) -cyano-L-alanine. Y ca. 100%. F. e. s. A. Climiak and J. J. Pastuszak, Chem. Ind. 1971, 427 with NH4-thiocyanate in the presence of 2-methylindole s. E. Wiinsdi and R. Spangenberg, B. 105, 740 (1972). 

The cycloalkylamine salts of 5-cyano-l-uracilacetic acid and analogues, exemplified by (LI), are claimed to produce marked inhibition of gastric secretion with virtually no anticholinergic activity [378]. This activity is not inherent in the free acetic acid nor in the amine. There is no distinction between optical isomers of the longer chain acids. The pyrimidine portion can be prepared by the treatment of a-cyano-/3-ethoxy-A -(ethoxycarbonyl)acrylamide with alanine or related derivatives [301,302]. 

When D,L-alanine and cir-chloroacrylonitrile are heated at +100°C in an excess of acetic anhydride, CO2 is evolved and 3-cyano-2,5-dimethylpyrrol (A) is isolated as sole reaction product in 70% yield. 

L-3-(3-Deoxy-l,2 5,6-di-0-isopropylidene-a-D-allofuranos-3-yl)alanine (290) (R = R = H) has been synthesized by a route that involved the addition of the carbanion derived from methyl (methylthio)methyl sulphoxide to 3-C-cyano-methyl-3-deoxy-l,2 5,6-di-0-isopropylidene-a-D-allofuranose. Subsequent treatment of the resulting (glycosyl)enamino sulphoxide with acetic anhydride, base-catalysed ester-exchange, and reductive desulphurization afforded the A-acetyl-3-(glycos-3-yl)alanate (290) (R = Ac R = Me), which was hydrolysed to (290) (R = R = H) with base. 

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)-... 

The molecular structure of B after irradiation is shown in Fig. 21. Only the 1-cyanoethyl group was changed after irradiation. The inverted 1-cyanoethyl group takes a different conformation from those observed in the piperidine and pyrrolidine crystals the methyl group is replaced with the cyano group in the alaninate crystal, whereas the methyl group is replaced with the hydrogen atom in the piperidine and pyrrolidine crystals. Such an inversion mode has been found only in a crystal of (l-cyanoethyl)(3-hydroxypyridine)cobaloxime [42]. 

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

---