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Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation.

Journal of industrial microbiology & biotechnology (2005-12-02)
Yanbin Liu, Qian Sha, Sheng Wu, Jianjun Wang, Liu Yang, Wanru Sun
ABSTRACT

A microorganism with the ability to catalyze the resolution of racemic phenyloxirane was isolated and identified as Aspergillus niger SQ-6. Chiral capillary electrophoresis was successfully applied to separate both phenyloxirane and phenylethanediol. The epoxide hydrolase (EH) involved in this resolution process was (R)-stereospecific and constitutively expressed. When whole cells were used during the biotransformation process, the optimum temperature and pH for stereospecific vicinal diol production were 35 degrees C and 7.0, respectively. After a 24-h conversion, the enantiomer excess of (R)-phenylethanediol produced was found to be >99%, with a conversion rate of 56%. In fed-batch fermentations at 30 degrees C for 44 h, glycerol (20 g L(-1)) and corn steep liquor (CSL) (30 g L(-1)) were chosen as the best initial carbon and nitrogen sources, and EH production was markedly improved by pulsed feeding of sucrose (2 g L(-1) h(-1)) and continuous feeding of CSL (1 g L(-1) h(-1)) at a fermentation time of 28 h. After optimization, the maximum dry cell weight achieved was 24.5+/-0.8 g L(-1); maximum EH production was 351.2+/-13.1 U L(-1) with a specific activity of 14.3+/-0.5 U g(-1). Partially purified EH exhibited a temperature optimum at 37 degrees C and pH optimum at 7.5 in 0.1 M phosphate buffer. This study presents the first evidence for the existence of a predicted epoxide racemase, which might be important in the synthesis of epoxide intermediates.

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%