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Microbial production of aliphatic (S)-epoxyalkanes by using Rhodococcus sp. strain ST-10 styrene monooxygenase expressed in organic-solvent-tolerant Kocuria rhizophila DC2201.

Applied and environmental microbiology (2015-01-04)
Hiroshi Toda, Takuya Ohuchi, Ryouta Imae, Nobuya Itoh
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Styrene, ReagentPlus®, contains 4-tert-butylcatechol as stabilizer, ≥99%
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Hexadecane, ReagentPlus®, 99%
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Dodecane, ReagentPlus®, ≥99%
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Hexadecane, anhydrous, ≥99%
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Hexadecane, analytical standard
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Tetradecane, olefin free, ≥99.0% (GC)
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Dodecane, analytical standard
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Dimethyl phthalate, ≥99%
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Diethyl phthalate, ≥99%
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Di-n-octyl phthalate, analytical standard
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6-Bromo-1-hexene, 95%
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Density Standard 749 kg/m3, H&D Fitzgerald Ltd. Quality
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1-Heptene, 97%
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Styrene solution, certified reference material, 200 μg/mL in methanol
Sigma-Aldrich
2-Methyl-1-hexene, 96%
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Di-n-octyl phthalate, analytical standard

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