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Enantioselective bioreductive preparation of chiral halohydrins employing two newly identified stereocomplementary reductases

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논문

Enantioselective bioreductive preparation of chiral halohydrins employing two newly identified stereocomplementary reductases

학술지

RSC advances

저자명

Xu, Guo-Chao; Yu, Hui-Lei; Shang, Yue-Peng; Xu, Jian-He

초록

Two robust stereocomplementary carbonyl reductases (<I>Dh</I>CR and<I>Cg</I>CR) were identified through rescreening the carbonyl reductase toolbox. Five reductases were returned through the activity and enantioselectivity assay for &alpha;-chloro-1-acetophenone and ethyl 4-chloro-3-oxo-butanate (COBE). Three reductases were stable at elevated substrate loading. Enzymatic characterization revealed that<I>Dh</I>CR and<I>Cg</I>CR were more thermostable. As much as 330 g COBE in 1 L biphasic reaction mixture was reduced to (<I>S</I>)- and (<I>R</I>)-3-hydroxy-4-chlorobutyrate by<I>Dh</I>CR and<I>Cg</I>CR (coexpressed with glucose dehydrogenase), with 92.5% and 93.0% yields, &amp;gt;99% ee, and total turnover numbers of 53 800 and 108 000, respectively. Six other &alpha;-halohydrins were asymmetrically reduced to optically pure forms at a substrate loading of 100 g L<SUP>&#x2212;1</SUP>. Our results indicate the potential of these two stereocomplementary reductases in the synthesis of valuable &alpha;-halohydrins for pharmaceuticals..

발행연도

2015

발행기관

The Royal Society of Chemistry

ISSN

2046-2069

5

29

페이지

pp.22703-22711

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논문; 2015-01-01

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