Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols

Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols

The present work reports the Metschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones an...

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Main Authors: Vachan Singh Meena, Linga Banoth, U. C. Banerjee
Format: Article
Language:English
Published: Hindawi Limited 2014-01-01
Series:BioMed Research International
Online Access:http://dx.doi.org/10.1155/2014/410530
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spelling doaj-e6873bac2b2a4ff28338a5a194b40d292020-11-24T21:20:09ZengHindawi LimitedBioMed Research International2314-61332314-61412014-01-01201410.1155/2014/410530410530Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-DiolsVachan Singh Meena0Linga Banoth1U. C. Banerjee2Department of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, IndiaDepartment of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, IndiaDepartment of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, IndiaThe present work reports the Metschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones and the reduction of the ketones to (S)-secondary alcohols. Method is applicable to a repertoire of racemic aryl secondary alcohols and 1,2-diols establishing a wide range of substrate specificity of M. koreensis. This ecofriendly method afforded the product in high yield (88%) and excellent optical purity (>98% ee), minimizing the requirement of multistep reaction and expensive cofactor.http://dx.doi.org/10.1155/2014/410530
collection DOAJ
language English
format Article
sources DOAJ
author Vachan Singh Meena
Linga Banoth
U. C. Banerjee
spellingShingle Vachan Singh Meena
Linga Banoth
U. C. Banerjee
Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
BioMed Research International
author_facet Vachan Singh Meena
Linga Banoth
U. C. Banerjee
author_sort Vachan Singh Meena
title Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
title_short Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
title_full Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
title_fullStr Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
title_full_unstemmed Demonstration of Redox Potential of Metschnikowia koreensis for Stereoinversion of Secondary Alcohols/1,2-Diols
title_sort demonstration of redox potential of metschnikowia koreensis for stereoinversion of secondary alcohols/1,2-diols
publisher Hindawi Limited
series BioMed Research International
issn 2314-6133
2314-6141
publishDate 2014-01-01
description The present work reports the Metschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones and the reduction of the ketones to (S)-secondary alcohols. Method is applicable to a repertoire of racemic aryl secondary alcohols and 1,2-diols establishing a wide range of substrate specificity of M. koreensis. This ecofriendly method afforded the product in high yield (88%) and excellent optical purity (>98% ee), minimizing the requirement of multistep reaction and expensive cofactor.
url http://dx.doi.org/10.1155/2014/410530
work_keys_str_mv AT vachansinghmeena demonstrationofredoxpotentialofmetschnikowiakoreensisforstereoinversionofsecondaryalcohols12diols
AT lingabanoth demonstrationofredoxpotentialofmetschnikowiakoreensisforstereoinversionofsecondaryalcohols12diols
AT ucbanerjee demonstrationofredoxpotentialofmetschnikowiakoreensisforstereoinversionofsecondaryalcohols12diols
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