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.
journal_name
Appl Biochem Biotechnoljournal_title
Applied biochemistry and biotechnologyauthors
Yu S,Li H,Lu Y,Zheng Gdoi
10.1007/s12010-017-2628-8subject
Has Abstractpub_date
2018-04-01 00:00:00pages
1319-1331issue
4eissn
0273-2289issn
1559-0291pii
10.1007/s12010-017-2628-8journal_volume
184pub_type
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