Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS-1

被引：15

作者：

Wu, Kailin ^{[1
]}

Tang, Linchao ^{[1
]}

Cui, Haibo ^{[1
]}

Wan, Nanwei ^{[1
]}

Liu, Ziyan ^{[1
]}

Wang, Zhongqiang ^{[1
]}

Zhang, Shimin ^{[1
]}

Cui, Baodong ^{[1
]}

Han, Wenyong ^{[1
]}

Chen, Yongzheng ^{[1
]}

机构：

[1] Zunyi Med Univ, Sch Pharm, Gener Drug Res Ctr Guizhou Prov, Green Pharmaceut Engn Res Ctr Guizhou Prov, Zunyi 563000, Peoples R China

来源：

CHEMCATCHEM | 2018年 / 10卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Biocatalysis; asymmetric sulfoxidation; P450; monooxygenases; enantiopure sulfoxide; DIRECTED EVOLUTION; MONOOXYGENASES; HYDROXYLATION; PERSPECTIVES; DEALKYLATION; CATALYST;

D O I：

10.1002/cctc.201801139

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Cytochrome P450 monooxygenases (P450s) catalyzed asymmetric sulfoxidation represents a green route for the synthesis of valuable enantiopure sulfoxides, which are potentially interesting synthons in synthetic and pharmaceutical chemistry. Here the potential P450 and redox partner genes from Parvibaculum lavamentivorans DS-1 are screened and co-expressed in Escherichia coli host to construct twenty recombinant P450 strains. By testing the whole-cell biooxidation of thioanisole, P450(PL2) (CYP278A4) and P450(PL7) (CYP108G3) are identified with excellent S enantioselectivity while P450(PL1) (CYP111B1) and P450(PL9) (CYP153A26) exhibit the complementary R enantioselectivity. Asymmetric sulfoxidation of sulfides 1a-1m is further investigated using the recombinant E. coli strain P450(PL2)-2 based on the optimal conditions, producing the corresponding enantioenriched sulfoxides with up to 82% isolated yield and 99% ee.

引用

页码：5410 / 5413

页数：4

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