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[1]盖萍,汤传根,刘静媛,等.氧化微杆菌C3催化3,5-双三氟甲基苯乙酮的不对称反-Prelog还原[英文][J].应用与环境生物学报,2013,19(01):37-42.[doi:10.3724/SP.J.1145.2013.00037]
 GAI Ping,TANG Chuangen,LIU Jingyuan,et al.Asymmetric anti-Prelog Reduction of 3,5-bis(trifluoromethyl)-acetophenone by Microbacterium oxydans C3[J].Chinese Journal of Applied & Environmental Biology,2013,19(01):37-42.[doi:10.3724/SP.J.1145.2013.00037]
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氧化微杆菌C3催化3,5-双三氟甲基苯乙酮的不对称反-Prelog还原[英文]()
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《应用与环境生物学报》[ISSN:1006-687X/CN:51-1482/Q]

卷:
19卷
期数:
2013年01期
页码:
37-42
栏目:
研究论文
出版日期:
2013-02-25

文章信息/Info

Title:
Asymmetric anti-Prelog Reduction of 3,5-bis(trifluoromethyl)-acetophenone by Microbacterium oxydans C3
作者:
盖萍汤传根刘静媛刘艳张超吴中柳
(1中国科学院环境与应用微生物重点实验室,中国科学院成都生物研究所 成都 610041)
(2四川省环境微生物重点实验室,中国科学院成都生物研究所 成都 610041)
(3中国科学院大学 北京 100049)
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)
关键词:
生物还原氧化微杆菌C3阿瑞匹坦(R)-35-双三氟甲基-1-苯乙醇
Keywords:
bioreduction Microbacterium oxydans C3 Aprepitant (R)-35-bis(trifluoromethyl)-1-phenethanol
分类号:
Q939.9
DOI:
10.3724/SP.J.1145.2013.00037
文献标志码:
A
摘要:
(R)-3,5-双三氟甲基-1-苯乙醇是合成神经激肽1受体拮抗剂阿瑞匹坦的关键手性醇中间体. 通过筛选得到一株氧化微杆菌C3(Microbacterium oxydans C3),其能不对称还原底物3,5-双三氟甲基苯乙酮为(R)-3,5-双三氟甲基-1-苯乙醇. 在底物浓度为5 g/L时,生物转化反应40 h,能达到>99%的ee值和95%的底物转化率. 底物浓度提高到50 g/L时,生物转化的ee值依然保持99%,并能达到56%的底物转化率. 利用该氧化微杆菌C3对其他含氟苯乙酮衍生物进行生物转化反应,同样得到了较高的立体选择性和底物转化率.
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.

参考文献/References:

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备注/Memo

备注/Memo:
Supported by the 100 Talents Program, the West Light Foundation, and the Knowledge Innovation Program (No. KSCX2-YW-G-075) of the Chinese Academy of Sciences, and the National Natural Science Foundation of China (Nos. 20802073, 21072183
更新日期/Last Update: 2013-02-26