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Issue 2, 2017
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New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with D-amino acid oxidase from porcine kidney

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Abstract

Oxidation of amino groups in amines or amino acids activates the sp3 Cα–H bond to form imines, making the alpha carbon atom a preferable target for nucleophilic reagents such as cyanide. Therefore, we focused on the oxidase reaction for the production of primary α-aminonitriles via imines. D-Amino acid oxidase from porcine kidney (pkDAO) and L-amino acid oxidase from Crotalus atrox catalyzed the synthesis of 2-amino-2-cyano-3-phenylpropanoic acid from phenylalanine and potassium cyanide (KCN). Mutant pkDAO (Y228L/R283G) catalyzed the synthesis of racemic-2-methyl-2-phenylglycinonitrile from (R)-α-methylbenzylamine and KCN. Based on these results, we developed a new cascade reaction for the synthesis of unnatural α-amino acids from primary amines using mutant pkDAO and nitrilase AY487533. This is the first report of the enzymatic synthesis of primary α-aminonitriles and unnatural α-amino acids. These methods will contribute widely to the synthesis of primary α-aminonitriles and unnatural α-amino acids in aqueous systems.

Graphical abstract: New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with d-amino acid oxidase from porcine kidney

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Publication details

The article was received on 22 Jul 2016, accepted on 31 Aug 2016 and first published on 14 Sep 2016


Article type: Paper
DOI: 10.1039/C6GC02003H
Citation: Green Chem., 2017,19, 418-424
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    New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with D-amino acid oxidase from porcine kidney

    N. Kawahara, K. Yasukawa and Y. Asano, Green Chem., 2017, 19, 418
    DOI: 10.1039/C6GC02003H

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