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A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone.
Appl Biochem Biotechnol 2018; 184(4):1319-1331AB

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+Show Affiliations

State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing, 100029, People's Republic of China.State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing, 100029, People's Republic of China.State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing, 100029, People's Republic of China.State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing, 100029, People's Republic of China. zhenggj@mail.buct.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29022160

Citation

Yu, Songzhu, et al. "A Catalyst From Burkholderia Cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone." Applied Biochemistry and Biotechnology, vol. 184, no. 4, 2018, pp. 1319-1331.
Yu S, Li H, Lu Y, et al. A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone. Appl Biochem Biotechnol. 2018;184(4):1319-1331.
Yu, S., Li, H., Lu, Y., & Zheng, G. (2018). A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone. Applied Biochemistry and Biotechnology, 184(4), pp. 1319-1331. doi:10.1007/s12010-017-2628-8.
Yu S, et al. A Catalyst From Burkholderia Cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone. Appl Biochem Biotechnol. 2018;184(4):1319-1331. PubMed PMID: 29022160.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone. AU - Yu,Songzhu, AU - Li,Hongxia, AU - Lu,Yan, AU - Zheng,Guojun, Y1 - 2017/10/12/ PY - 2017/05/19/received PY - 2017/10/03/accepted PY - 2017/10/13/pubmed PY - 2018/7/11/medline PY - 2017/10/13/entrez KW - 3, 5-Bis(trifluoromethyl) acetophenone KW - Anti-Prelog’s KW - Aprepitant KW - Burkholderia cenocepacia KW - Carbonyl reductase SP - 1319 EP - 1331 JF - Applied biochemistry and biotechnology JO - Appl. Biochem. Biotechnol. VL - 184 IS - 4 N2 - (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. SN - 1559-0291 UR - https://www.unboundmedicine.com/medline/citation/29022160/A_Catalyst_from_Burkholderia_cenocepacia_for_Efficient_Anti_Prelog's_Bioreduction_of_35_Bis_Trifluoromethyl__Acetophenone_ L2 - https://dx.doi.org/10.1007/s12010-017-2628-8 DB - PRIME DP - Unbound Medicine ER -