Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 16, Pages 3443-3450Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400383
Keywords
alkenes; asymmetric epoxidation; biosynthesis; enzyme catalysis; styrene monooxygenase
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We describe the enantioselective epoxidation of straight-chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST-10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1-hexene to (S)-1,2-epoxyhexane (>44.6 mM) using 2-propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di- and tri-substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)-epoxyalkanes.
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