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Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system

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

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system

학술지

Catalysis science & technology

저자명

Yang, Zeyu; Fu, Hengwei; Ye, Wenjie; Xie, Youyu; Liu, Qinghai; Wang, Hualei; Wei, Dongzhi

초록

<P>Alcohol dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asymmetric synthesis of chiral alcohols; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the by-product, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene <I>smadh</I>2 was identified from <I>Stenotrophomonas maltophilia</I> by traditional genome mining technology. The gene was cloned into <I>Escherichia coli</I> cells and then expressed to yield <I>Sm</I>ADH2. <I>Sm</I>ADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, v/v) concentration. Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the by-product acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcohols are synthesised at a high substrate loading (@@>@@150 g L<SUP>&#x2212;1</SUP>) without adding external coenzymes. Among these, about 780 g L<SUP>&#x2212;1</SUP> (6 M) ethyl acetoacetate is completely converted into ethyl (<I>R</I>)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L<SUP>&#x2212;1</SUP> d<SUP>&#x2212;1</SUP> space-time yield. Molecular dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance <I>Sm</I>ADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcohols on an industrial scale.</P>

발행연도

2020

발행기관

The Royal Society of Chemistry

ISSN

2044-4753

ISSN

2044-4761

10

1

페이지

pp.70-78

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1 2023-12-11
3 2023-12-11

논문; 2020-12-31

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