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Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles

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

Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles

학술지

Organic letters

저자명

Liardo, Elisa; Rí os-Lombardí a, Nicolá s; Morí s, Francisco; Gonzá lez-Sabí n, Javier; Rebolledo, Francisca

초록

<P>A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of <I>Rhodococcus rhodochrous</I> provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2016/orlef7.2016.18.issue-14/acs.orglett.6b01510/production/images/medium/ol-2016-015107_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol6b01510'>ACS Electronic Supporting Info</A></P>

발행연도

2016

발행기관

American Chemical Society

ISSN

1523-7060

18

14

페이지

pp.3366-3369

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논문; 2016-12-31

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