Premium
Whole‐cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: ( S )‐5‐Chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1 H ‐indene‐2‐carboxylic acid methyl ester
Author(s) -
Zhang Yinjun,
Zhang Hongyun,
Cheng Feifei,
Xia Ying,
Zheng Jianyong,
Wang Zhao
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23124
Subject(s) - chemistry , indene , substrate (aquarium) , indoxacarb , hydrolysis , alicyclic compound , biocatalysis , stereoselectivity , strain (injury) , carboxylic acid , organic chemistry , stereochemistry , cereus , bacillus cereus , reaction mechanism , catalysis , bacteria , medicine , oceanography , pesticide , agronomy , biology , geology , genetics
In this study, a newly isolated strain screened from the indoxacarb‐rich agricultural soils, Bacillus cereus WZZ006, has a high stereoselectivity to racemic substrate 5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1 H ‐indene‐2‐carboxylic acid methyl ester. ( S )‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1 H ‐indene‐2‐carboxylic acid methyl ester was obtained by bio‐enzymatic resolution. After the 36‐hour hydrolysis in 50‐mM racemic substrate under the optimized reaction conditions, the e.e . s was up to 93.0% and the conversion was nearly 53.0% with the E being 35.0. Therefore, B cereus WZZ006 performed high‐level ability to produce ( S )‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1 H ‐indene‐2‐carboxylic acid methyl ester. This study demonstrates a new biocatalytic process route for preparing the indoxacarb chiral intermediates and provides a theoretical basis for the application of new insecticides in agricultural production.