|Table of Contents|

Asymmetric anti-Prelog Reduction of 3,5-bis(trifluoromethyl)-acetophenone by Microbacterium oxydans C3(PDF)

Chinese Journal of Applied & Environmental Biology[ISSN:1006-687X/CN:51-1482/Q]

Issue:
2013 01
Page:
37-42
Research Field:
Articles
Publishing date:

Info

Title:
Asymmetric anti-Prelog Reduction of 3,5-bis(trifluoromethyl)-acetophenone by Microbacterium oxydans C3
Author(s):
GAI PingTANG ChuangenLIU JingyuanLIU YanZHANG ChaoWU Zhongliu
(1Key Laboratory of Environmental and Applied Microbiology of Chinese Academy of Sciences, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China)
(2Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China)
(3University of Chinese Academy of Sciences, Beijing 100049, China)
Keywords:
bioreduction Microbacterium oxydans C3 Aprepitant (R)-35-bis(trifluoromethyl)-1-phenethanol
CLC:
Q939.9
PACS:
DOI:
10.3724/SP.J.1145.2013.00037
DocumentCode:

Abstract:
The isolated microorganism Microbacterium oxydans C3 reduced 3,5-bis(trifluoromethyl)-acetophenone at 5 g/L to (R)-3,5-bis(trifluoromethyl)-1-phenethanol, a pharmaceutically alcohol intermediate for the synthesis of Aprepitant, a potent human NK-1 receptor antagonists, in 40 h. The bioreaction had desirable enantioselectivity (> 99% enantiomeric excess [ee]) and 95% conversion. When the substrate concentration reached 50 g/L, the bioreaction afforded (R)-3,5-bis(trifluoromethyl)-1-phenethanlo with 56% conversion and 99% ee. The usefulness of M. oxydans C3 was further demonstrated by the bioreduction of several fluorinated acetophenones with good conversion and excellent enantioselectivity.

References

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Last Update: 2013-02-26