Biocatalytic application of nitrilases from Fusarium solani O1 and Aspergillus niger K10

The nitrilases from Fusarium solani O1 and Aspergillus niger K10 showed a broad substrate specificity for carbocyclic and nonaromatic heterocyclic amino nitriles, the preferred substrates being five-membered gamma-amino nitrile (+/-)-1a, six-membered gamma-amino nitriles (+/-)-3a, (+/-)-5a and (+/-)-6a, pyrrolidine-3-carbonitriles (+/-)-9a and (+/-)-10a as well as piperidine-4-carbonitriles 14a and 15a. Both enzymes showed a strong diastereopreference for cis- vs. trans-gamma-amino nitriles. The electronic and steric effects of N-protecting groups affected the reactivity of the nitriles. Amides as by-products of the nitrilase-catalyzed reaction were produced from heterocyclic amino nitriles (+/-)-9a, (+/-)-10a, 14a and 15a by the A. niger enzyme but only from nitrile (+/-)-9a by the F. solani enzyme. (C) 2008 Elsevier B.V. All rights reserved.