title: Microbial production of aliphatic (S)-epoxyalkanes by using Rhodococcus sp. strain ST-10 styrene monooxygenase expressed in organic-solvent-tolerant Kocuria rhizophila DC2201.
abstract: We describe the development of biocatalysis for producing optically pure straight-chain (S)-epoxyalkanes using styrene monooxygenase of Rhodococcus sp. strain ST-10 (RhSMO). RhSMO was expressed in the organic solvent-tolerant microorganism Kocuria rhizophila DC2201, and the bioconversion reaction was performed in an organic solvent-water biphasic reaction system. The biocatalytic process enantioselectively converted linear terminal alkenes to their corresponding (S)-epoxyalkanes using glucose and molecular oxygen. When 1-heptene and 6-chloro-1-hexene were used as substrates (400 mM) under optimized conditions, 88.3 mM (S)-1,2-epoxyheptane and 246.5 mM (S)-1,2-epoxy-6-chlorohexane, respectively, accumulated in the organic phase with good enantiomeric excess (ee; 84.2 and 95.5%). The biocatalysis showed broad substrate specificity toward various aliphatic alkenes, including functionalized and unfunctionalized alkenes, with good to excellent ee. Here, we demonstrate that this biocatalytic system is environmentally friendly and useful for producing various enantiopure (S)-epoxyalkanes.
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Kurokawa, Imizu, Toyama, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Toda
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Kurokawa, Imizu, Toyama, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Ohuchi
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Kurokawa, Imizu, Toyama, Japan.
authors.forename: Ryouta
authors.initials: R
authors.lastname: Imae
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Kurokawa, Imizu, Toyama, Japan nbito@pu-toyama.ac.jp.
authors.forename: Nobuya
authors.initials: N
authors.lastname: Itoh
mesh_terms: D000473:Alkanes / Q000378:metabolism*; D001711:Biotransformation; D015870:Gene Expression; D005947:Glucose / Q000378:metabolism; D016982:Micrococcus luteus / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism*; D010100:Oxygen / Q000378:metabolism; D010105:Oxygenases / Q000235:genetics / Q000378:metabolism*; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism; D012240:Rhodococcus / Q000201:enzymology* / Q000235:genetics; D013379:Substrate Specificity
chemical_list: D000473:Alkanes; D011994:Recombinant Proteins; D010105:Oxygenases; C026721:styrene monooxygenase; D005947:Glucose; D010100:Oxygen