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Enantioselective Resolution of (±)-1-Phenylethanol and (±)-1-Phenylethyl Acetate by a Novel Esterase From Bacillus Sp. SCSIO 15121

Enantioselective Resolution of (±)-1-Phenylethanol and (±)-1-Phenylethyl Acetate by a Novel Esterase From Bacillus Sp. SCSIO 15121

Jiayuan Liang, Yun Zhang, Aijun Sun, Dun Deng, Yunfeng Hu

Appl Biochem Biotechnol. 2016 Feb;178(3):558-75.

PMID: 26467742

Abstract:

A novel microbial esterase BSE01281 identified from the Indian Ocean was cloned, expressed, and functionally characterized. Esterase BSE01281 could enanoselectively resolve (±)-1-phenylethanol and (±)-1-phenylethyl acetate through two types of enzymatic reactions. After the optimization of enzymatic reactions, BSE01281 could efficiently generate (R)-1-phenylethyl acetate with high enantiomeric excess (>99%) and high conversion (42%) after 96 h trans-esterification reactions. Additionally, BSE01281 could also produce (R)-1-phenylethanol (e.e. > 99%) and (S)-1-phenylethyl acetate (e.e. > 95%) at a conversion of 49% through direct hydrolysis of inexpensive racemic 1-phenylethyl acetate for 8 h. Optically pure (R)-1-phenylethanol generated from direct enzymatic hydrolysis of racemic 1-phenylethyl acetate by BSE01281 is not easily prepared by dehydrogenases, which generally follow the "Prelog's rule" and give (S)-1-phenylethanol instead.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1445916	(S)-(−)-1-Phenylethanol		1445-91-6	Price

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