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Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

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논문

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

학술지

Advanced synthesis & catalysis

저자명

Mé ndez‐ Sá nchez, Daniel; Mangas‐ Sá nchez, Juan; Busto, Eduardo; Gotor, Vicente; Gotor‐ Ferná ndez, Vicente

초록

<P><B>Abstract</B></P><P>Dynamic reductive kinetic resolutions of racemic 3&#8208;arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from <I>Rhodococcus ruber</I> DSM 44541 overexpressed in <I>Escherichia coli</I> (<I>E. coli</I>/ADH&#8208;A) and the commercially available evo&#8208;1.1.200, while the Amberlite IRA&#8208;440 C and the DOWEX&#8208;MWA&#8208;1 resins allowed efficient <I>in situ</I> racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (<I>R</I>,<I>R</I>)&#8208;substituted propan&#8208;2&#8208;ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan&#8208;2&#8208;ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.</P>

발행연도

2016

발행기관

WILEY&#x2010;VCH Verlag

라이선스

cc-by-nc-nd

ISSN

1615-4150

ISSN

1615-4169

358

1

페이지

pp.122-131

주제어

alcohol dehydrogenases; dynamic processes; dynamic reductive kinetic resolutions; ion exchange resins; ketones

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1 2023-12-11

논문; 2016-01-05

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