Cyclohexylamine oxidase as useful biocatalyst for the kinetic resolution and dereacemization of amines

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DOIResolve DOI: http://doi.org/10.1139/V11-086
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TypeArticle
Journal titleCanadian Journal of Chemistry
Volume90
Issue1
Pages3945; # of pages: 7
Subjectbiocatalysis; cyclohexylamine oxidase; chiral amines; kinetic resolution; deracemization; biocatalyseur; oxydase de la cyclohexylamine; amines chirales; résolution cinétique; déracémisation
AbstractThe 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 ?-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 borane-ammonia 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.
Publication date
LanguageEnglish
AffiliationNRC Biotechnology Research Institute; National Research Council Canada
Peer reviewedYes
NRC number53377
NPARC number19304695
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Record identifierddb28c81-104c-406a-84e7-418332bfeb72
Record created2012-03-06
Record modified2016-05-09
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