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논문 기본 정보
- 자료유형
- 학술저널
- 저자정보
- 저널정보
- 한국미생물생명공학회 Journal of Microbiology and Biotechnology Journal of Microbiology and Biotechnology 제23권 제3호
- 발행연도
- 2013.1
- 수록면
- 343 - 350 (8page)
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초록· 키워드
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(R)-[3,5-Bis(trifluoromethyl)phenyl] ethanol is a key chiral intermediate for the synthesis of aprepitant. In this paper, an efficient synthetic process for (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone,catalyzed by Leifsonia xyli CCTCC M 2010241 cells using isopropanol as the co-substrate for cofactor recycling. Firstly,the substrate and product solubility and cell membrane permeability of biocatalysts were evaluated with different co-substrate additions into the reaction system, in which isopropanol manifested as the best hydrogen donor of coupled NADH regeneration during the bioreduction of 3,5-bis(trifluoromethyl) acetophenone. Subsequently, the optimization of parameters for the bioreduction were undertaken to improve the effectiveness of the process.
The determined efficient reaction system contained 200mM of 3,5-bis(trifluoromethyl) acetophenone, 20% (v/v) of isopropanol, and 300 g/l of wet cells. The bioreduction was executed at 30oC and 200 rpm for 30 h, and 91.8% of product yield with 99.9% of enantiometric excess (e.e.)was obtained. The established bioreduction reaction system could tolerate higher substrate concentrations of 3,5-bis(trifluoromethyl) acetophenone, and afforded a satisfactory yield and excellent product e.e. for the desired (R)-chiral alcohol, thus providing an alternative to the chemical synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol.
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참고문헌 (20)
참고문헌 신청
Asako, H / 2010 / Biocatalytic reduction system for the production of chiral methyl (R)/(S)-4-bromo-3-hydroxybutyrate / Tetrahedron Lett 51 : 2664 ~ 2666
Barros-Filho, B. A / 2010 / Bioreduction of prochiral ketones by growing cells of Lasiodiplodia theobromae: Discovery of a versatile biocatalyst for asymmetric synthesis / J.
Gelo-Pujic, M / 2006 / Microbial and homogenous asymmetric catalysis in the reduction of 1- [3,5-bis(trifluoromethyl)phenyl]ethanone / Tetrahedron Asymmetry 17 : 2000 ~ 2005
Goldberg, K / 2007 / Biocatalytic ketone reduction - a powerful tool for the production of chiral alcohols - part II: Whole-cell reductions / Appl. Microbiol. Biotechnol 76 :
Hansen, K. B / 2003 / Scalable, efficient process for the synthesis of (R)-3,5-bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation
Barros-Filho, B. A / 2010 / Bioreduction of prochiral ketones by growing cells of Lasiodiplodia theobromae: Discovery of a versatile biocatalyst for asymmetric synthesis / J.
Gelo-Pujic, M / 2006 / Microbial and homogenous asymmetric catalysis in the reduction of 1- [3,5-bis(trifluoromethyl)phenyl]ethanone / Tetrahedron Asymmetry 17 : 2000 ~ 2005
Goldberg, K / 2007 / Biocatalytic ketone reduction - a powerful tool for the production of chiral alcohols - part II: Whole-cell reductions / Appl. Microbiol. Biotechnol 76 :
Hansen, K. B / 2003 / Scalable, efficient process for the synthesis of (R)-3,5-bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation
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