Abstract
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 γ-amino nitrile (±)- 1a, six-membered γ-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-γ-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.
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