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Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS‐1
Author(s) -
Wu Kailin,
Tang Linchao,
Cui Haibo,
Wan Nanwei,
Liu Ziyan,
Wang Zhongqiang,
Zhang Shimin,
Cui Baodong,
Han Wenyong,
Chen Yongzheng
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801139
Subject(s) - thioanisole , enantiopure drug , cytochrome p450 , biocatalysis , chemistry , monooxygenase , escherichia coli , stereochemistry , recombinant dna , synthon , yield (engineering) , enantioselective synthesis , combinatorial chemistry , enzyme , organic chemistry , biochemistry , catalysis , gene , reaction mechanism , materials science , metallurgy
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 1 a–1 m 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 .
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