Applied Biochemistry and Biotechnology, Vol.178, No.3, 558-575, 2016
Enantioselective Resolution of (+/-)-1-Phenylethanol and (+/-)-1-Phenylethyl Acetate by a Novel Esterase from Bacillus sp SCSIO 15121
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.
Keywords:Esterase;Kinetic resolution;Chiral 1-phenylethanol;Chiral 1-phenylethyl acetate;High enantiomeric excess