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Asymmetric biocatalytic reduction of 3,5-bis(trifluoromethyl) acetophenone to (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol using whole cells of newly isolated Leifsonia xyli HS0904

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Abstract

A novel bacterial strain HS0904 was isolated from a soil sample using 3,5-bis(trifluoromethyl) acetophenone as the sole carbon source. This bacterial isolate can asymmetrically reduce 3,5-bis(trifluoromethyl) acetophenone to (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol with high enantiometric excess (ee) value. Based on its morphological, physiological characteristics, Biolog, 16S rDNA sequence and phylogenetic analysis, strain HS0904 was identified as Leifsonia xyli HS0904. To our knowledge, this is the first reported case on the species L. xyli exhibited R-stereospecific carbonyl reductase and used for the preparation of chiral (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol. The optimization of parameters for microbial transformation of 3,5-bis(trifluoromethyl) acetophenone to (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol catalyzed by whole cells of L. xyli HS0904 was carried out by examining some key factors including buffer pH, reaction temperature, shaking speed, substrate concentration, and reaction time. The obtained optimized conditions for the bioreduction are as follows: buffer pH 8.0, 70 mM of 3,5-bis(trifluoromethyl) acetophenone, 100 g l−1 of glucose as co-substrate, 200 g l−1 of resting cells as biocatalyst, reaction for 30 h at 30 °C and 200 rpm. Under above conditions, 99.4% of product ee and best yield of 62% were obtained, respectively. The results indicated that isolate L. xyli HS0904 is a novel potential biocatalyst for the production of (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol.

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Acknowledgments

This work was financially supported by grants from National Natural Science Foundation (21076193), People's Republic of China, and the Foundation of Zhejiang Key Developing Discipline of Pharmacy (20100609), Zhejiang Province, People's Republic of China.

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  1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, People’s Republic of China

    Pu Wang, Jin-Bo Cai, Qi Ouyang, Jun-Yao He & Hui-Zhen Su

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  1. Pu Wang
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  2. Jin-Bo Cai
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  3. Qi Ouyang
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  4. Jun-Yao He
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  5. Hui-Zhen Su
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Correspondence to Pu Wang.

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Wang, P., Cai, JB., Ouyang, Q. et al. Asymmetric biocatalytic reduction of 3,5-bis(trifluoromethyl) acetophenone to (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol using whole cells of newly isolated Leifsonia xyli HS0904. Appl Microbiol Biotechnol 90, 1897–1904 (2011). https://doi.org/10.1007/s00253-011-3233-3

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  • DOI: https://doi.org/10.1007/s00253-011-3233-3

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