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Demonstration of redox potential of Metschnikowia koreensis for stereoinversion of secondary alcohols/1,2-diols.

Meena VS, Banoth L, Banerjee UC - Biomed Res Int (2014)

Bottom Line: 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.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.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, India.

ABSTRACT
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.

Show MeSH
Stereoinversion of 3-aryloxy-1,2-propanediols by the whole cells of Metschnikowia koreensis.
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sch2: Stereoinversion of 3-aryloxy-1,2-propanediols by the whole cells of Metschnikowia koreensis.

Mentions: In this paper, a single whole cell biocatalyst (one pot) was successfully demonstrated for stereoinversion of aryl secondary alcohols (Scheme 1) and 1,2-diols (Scheme 2) to enantiopure (S)-alcohols in excellent yield and enantioselectivity. The present work is an attempt to combine the multienzyme reactions into single-step reactions, while minimizing the conventional drawbacks of catalysis.


Demonstration of redox potential of Metschnikowia koreensis for stereoinversion of secondary alcohols/1,2-diols.

Meena VS, Banoth L, Banerjee UC - Biomed Res Int (2014)

Stereoinversion of 3-aryloxy-1,2-propanediols by the whole cells of Metschnikowia koreensis.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3921931&req=5

sch2: Stereoinversion of 3-aryloxy-1,2-propanediols by the whole cells of Metschnikowia koreensis.
Mentions: In this paper, a single whole cell biocatalyst (one pot) was successfully demonstrated for stereoinversion of aryl secondary alcohols (Scheme 1) and 1,2-diols (Scheme 2) to enantiopure (S)-alcohols in excellent yield and enantioselectivity. The present work is an attempt to combine the multienzyme reactions into single-step reactions, while minimizing the conventional drawbacks of catalysis.

Bottom Line: 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.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.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, India.

ABSTRACT
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.

Show MeSH