Abstract:The biocatalytic performance of a cloned cyclohexylamine oxidase derived from Brevibacterium oxydans IH-35A towards structurally different amines was investigated. Cycloalkyl primary amines, alkyl aryl amines, and a-carbon-substituted aliphatic amines were identified as suitable substrates for the biocatalyst based on an activity assay. Kinetic resolutions of several amines by either recombinant whole cells or crude enzyme extracts prepared therefrom gave enantiomerically pure (R)-amines besides the corresponding ketones. When cyclohexylamine oxidase in combination with a boraneammonia complex as reducing agent was applied to the deracemization of several substrates, excellent enantiomeric ratios (>99:1) and good isolated yields (62%-75%) of the corresponding (R)-amines were obtained.Key words: biocatalysis, cyclohexylamine oxidase, chiral amines, kinetic resolution, deracemization.Résumé : On a étudié la performance biocatalytique d'un clone de l'oxydase de la cyclohexylamine dérivé du Brevibacterium oxydans IH-35A vis-à-vis des amines de structures diverses. Sur la base d'un essai d'activité, il a été possible d'identifier les cycloalkylamines primaires, les alkylarylamines primaires et les amines aliphatiques portant un substituant sur le carbone en a comme des substrats appropriés pour le biocatalyseur. Les résolutions cinétiques de plusieurs amines par des cellules recombinantes complètes ou des extraits bruts d'enzyme préparés à partir de celles-ci conduisent à des amines (R) énantiomériquement pures aux côtés des cétones correspondantes. On a utilisé l'oxydase de la cyclohexylamine en combinaison avec un complexe de borane-ammoniac comme agent réducteur pour effectuer la déracémisation de plusieurs substrats, avec d'excellents rapports énantiomériques (>99/1) et de bons rendements en produits isolés (72 % à 75 %) des amines (R) correspondantes.
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