Search

Development of an enzymatic process for the synthesis of (S)-2-chloro-1-(2,4-dichlorophenyl) ethanol

메타 데이터

바이오화학분류
    • 바이오정밀화학
      1. 용매
    • 화장품용 기능성소재
      1. 기능성
      2. 계면활성제⁄증점제
    • 의료용 화학소재
      1. 치료제
      2. 식품첨가제
논문

Development of an enzymatic process for the synthesis of (S)-2-chloro-1-(2,4-dichlorophenyl) ethanol

학술지

Organic process research & development

저자명

Wei, Teng-Yun; Tang, Jia-Wei; Ni, Guo-Wei; Wang, Hong-Yi; Yi, Dong; Zhang, Fu-Li; Chen, Shao-Xin

초록

<P>(<I>S</I>)-2-Chloro-1-(2,4-dichlorophenyl) ethanol (<B>3</B>) is a chiral intermediate in the synthesis of luliconazole (<B>(<I>R</I>)-<I>E</I>-1</B>). Here, we report a novel biopreparation of <B>3</B> by bioreduction of 2-chloro-1-(2,4-dichlorophenyl) ethanone (<B>2</B>) using recombinant <I>Escherichia coli</I> expressing LK08, a ketoreductase mutant from <I>Lactobacillus kefiri</I>, as a biocatalyst. The reaction conditions for the biotransformation including pH, temperature, and concentration of isopropanol and NADP<SUP>+</SUP>, as well as the amount of recombinant <I>E. coli</I> cells, were optimized to improve the process productivity. When the enzymatic process was carried out on a 300 g scale under the optimized conditions, the ketone <B>2</B> was fully converted to chiral alcohol <B>3</B> with a product ee value of >99%. Furthermore, <B>3</B> was isolated and used to chemically synthesize luliconazole with 38% yield and 99% ee. This study presents an efficient and cost-effective chemoenzymatic process for the production of <B>(<I>R</I>)-<I>E</I>-1</B>.</P><BR>[FIG OMISSION]</BR>

발행연도

2019

발행기관

American Chemical Society

ISSN

1083-6160

ISSN

1520-586x

23

9

페이지

pp.1822-1828

주제어

(S)-2-chloro-1-(2,4-dichlorophenyl) ethanol; luliconazole; ketoreductase; biocatalysis; Lactobacillus kefiri

0건의 논문이 있습니다.

0건의 특허가 있습니다.

0건의 무역이 있습니다.

2건의 후보군 물질이 있습니다.

2 2023-12-11

논문; 2019-12-31

Export

About

Search

Trend