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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.
Appl Microbiol Biotechnol 2011; 90(6):1897-904AM

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.

Authors+Show Affiliations

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, People's Republic of China. wangpu@zjut.edu.cnNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21614678

Citation

Wang, Pu, 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." Applied Microbiology and Biotechnology, vol. 90, no. 6, 2011, pp. 1897-904.
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. 2011;90(6):1897-904.
Wang, P., Cai, J. B., Ouyang, Q., He, J. Y., & Su, H. Z. (2011). 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. Applied Microbiology and Biotechnology, 90(6), pp. 1897-904. doi:10.1007/s00253-011-3233-3.
Wang P, 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. 2011;90(6):1897-904. PubMed PMID: 21614678.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Wang,Pu, AU - Cai,Jin-Bo, AU - Ouyang,Qi, AU - He,Jun-Yao, AU - Su,Hui-Zhen, Y1 - 2011/03/29/ PY - 2011/01/30/received PY - 2011/03/03/accepted PY - 2011/03/01/revised PY - 2011/5/27/entrez PY - 2011/5/27/pubmed PY - 2011/9/8/medline SP - 1897 EP - 904 JF - Applied microbiology and biotechnology JO - Appl. Microbiol. Biotechnol. VL - 90 IS - 6 N2 - 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. SN - 1432-0614 UR - https://www.unboundmedicine.com/medline/citation/21614678/Asymmetric_biocatalytic_reduction_of_35_bis_trifluoromethyl__acetophenone_to__1R__[35_bis_trifluoromethyl_phenyl]_ethanol_using_whole_cells_of_newly_isolated_Leifsonia_xyli_HS0904_ L2 - https://dx.doi.org/10.1007/s00253-011-3233-3 DB - PRIME DP - Unbound Medicine ER -