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  • Enhancement of Candida parapsilosis catalyzing deracemization of (R,S)-1-phenyl-1,2-ethanediol to its (S)-enantiomer by a highly productive "two-in-one" resin-based in situ product removal strategy.

Enhancement of Candida parapsilosis catalyzing deracemization of (R,S)-1-phenyl-1,2-ethanediol to its (S)-enantiomer by a highly productive "two-in-one" resin-based in situ product removal strategy.

Bioresource technology (2010-06-25)
Qingsen Hu, Yan Xu, Yao Nie
ABSTRACT

In this study, a highly efficient process for Candida parapsilosis-catalyzed deracemization of racemic 1-phenyl-1,2-ethanediol (PED) was described, based on a resin-based in situ substrate feeding and product removal (ISSFPR) methodology. The resin H103 was selected and used to keep the combined concentration of (R)-PED and (S)-PED at about 15g/l in aqueous phase. In the presence of 143g/l H103 resin, 50g/l of racemic substrate was converted to (S)-PED with 99.3% enantiomeric excess (ee) in 92% yield, while the initial reaction could afford an ee>99% only when the substrate concentration was 15g/l or lower. To our knowledge, this was the first report on the application of a resin-based ISSFPR technique for enhancing the efficiency of microbial stereoinversion.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-(−)-1-Phenyl-1,2-ethanediol, 99%
Sigma-Aldrich
1-Phenyl-1,2-ethanediol, 97%
Sigma-Aldrich
(S)-(+)-1-Phenyl-1,2-ethanediol, 99%