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Bioproduction of Chiral Epoxyalkanes using Styrene Monooxygenase from Rhodococcus sp. ST‐10 (RhSMO)
Author(s) -
Toda Hiroshi,
Imae Ryouta,
Itoh Nobuya
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400383
Subject(s) - chemistry , bioproduction , biocatalysis , enantiomeric excess , enantioselective synthesis , styrene , monooxygenase , substrate (aquarium) , rhodococcus , enantiomer , alcohol dehydrogenase , organic chemistry , stereochemistry , alcohol , combinatorial chemistry , catalysis , enzyme , reaction mechanism , biochemistry , copolymer , polymer , oceanography , cytochrome p450 , geology
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.