Demonstration of Redox Potential ofMetschnikowia koreensisfor Stereoinversion of Secondary Alcohols/1,2-Diols
Author(s) -
Vachan Singh Meena,
Linga Banoth,
Uttam Chand Banerjee
Publication year - 2014
Publication title -
biomed research international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 126
eISSN - 2314-6141
pISSN - 2314-6133
DOI - 10.1155/2014/410530
Subject(s) - chemistry , stereoselectivity , cofactor , redox , yield (engineering) , enantiomeric excess , organic chemistry , aryl , stereochemistry , combinatorial chemistry , catalysis , enzyme , enantioselective synthesis , materials science , alkyl , metallurgy
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom