Biocatalytic application of nitrilases from Fusarium solani O1 and Aspergillus niger K10 |
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Authors: | Margit Winkler, Ond ej Kaplan, Vojt ch Vejvoda, Norbert Klempier,Ludmila Martí nkov |
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Affiliation: | aInstitute of Organic Chemistry, Graz University of Technology, A-8010 Graz, Stremayrgasse 16, Austria;bInstitute of Microbiology, Centre of Biocatalysis and Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20 Prague 4, Czech Republic |
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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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Keywords: | Amino nitriles Nitrilase Substrate specificity Enantioselectivity Diastereoselectivity |
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