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Enzyme Microb Technol. 2020 Jan;132:109391. doi: 10.1016/j.enzmictec.2019.109391. Epub 2019 Aug 11.

Functional characterization of an (R)-selective styrene monooxygenase from streptomyces sp. NRRL S-31.

Author information

1
Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China; Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu 610041, China; University of Chinese Academy of Sciences, Beijing 100049, China.
2
Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China; Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu 610041, China.
3
College of Life Sciences, Henan Agricultural University, 95 Wenhua Road, Zhengzhou 450002, China.
4
Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China; Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu 610041, China. Electronic address: wuzhl@cib.ac.cn.

Abstract

Styrene monooxygenases (SMOs) are two-component enzymes known to catalyze the epoxidation of styrene to (S)-styrene oxide. In this work, we identified a new oxygenase component, named StStyA, from the genome of Streptomyces sp. NRRL S-31. StStyA displayed complementary stereoselectivity to all of the known SMOs when coupled with a known reductase component (PsStyB), which made it the first natural SMO that produces (R)-styrene oxide. Accordingly, a plasmid co-expressing StStyA and PsStyB was constructed, which led to an artificial two-component SMO, named StStyA/B. When applied in the bio-epoxidation of nine aromatic alkenes, the enzyme showed activity toward five alkenes, and consistently displayed (R)-selectivity. Excellent stereoselectivity was achieved for all five substrates with enantiomeric excesses ranging from 91% to >99%ee.

KEYWORDS:

Asymmetric synthesis; Chiral epoxide; Epoxidation; Monooxygenase; Styrene oxide

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