A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone.

Abstract:

:(R)-3, 5-Bis(trifluoromethyl)phenyl ethanol is a key chiral intermediate for the synthesis of aprepitant. Through a genome mining approach, an NADPH-dependent short-chain dehydrogenases derived from Burkholderia cenocepacia (Bc-SDR) was discovered with excellent anti-Prelog's stereoselectivity of reducing 3, 5-bis(trifluoromethyl) acetophenone. The enzyme with 247 amino acids was successfully expressed in Escherichia coli and the molecular weight was about 26 kDa. Optimization of reaction conditions showed that the optimum temperature and pH of the enzyme was 25 °C and pH 7.0, respectively. Strong enhancement of enzyme activity was observed in the presence of 1 mM Mn2+. In addition, Bc-SDR exhibited (R)-selective enantioselectivity toward acetophenone derivatives, which makes it a potential catalyst for obtaining aromatic chiral alcohols as useful blocks in pharmaceutical applications.

authors

Yu S,Li H,Lu Y,Zheng G

doi

10.1007/s12010-017-2628-8

subject

Has Abstract

pub_date

2018-04-01 00:00:00

pages

1319-1331

issue

4

eissn

0273-2289

issn

1559-0291

pii

10.1007/s12010-017-2628-8

journal_volume

184

pub_type

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