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

Volumn 90, Issue 6, 2011, Pages 1897-1904

  Wang, Pu ^a   Cai, Jin Bo ^a   Ouyang, Qi ^a   He, Jun Yao ^a   Su, Hui Zhen ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

(1R) 3,5 bis(trifluoromethyl)phenyl ethanol; Bioreduction; Identification; Isolation; Leifsonia xyli HS0904

Indexed keywords

(1R)-[3,5-BIS(TRIFLUOROMETHYL)PHENYL] ETHANOL; 16S RDNA SEQUENCE; ACETOPHENONES; BACTERIAL ISOLATES; BACTERIAL STRAINS; BIOREDUCTIONS; BUFFER PH; CARBONYL REDUCTASE; CO-SUBSTRATE; ENANTIOMETRIC EXCESS; ISOLATION; KEY FACTORS; LEIFSONIA XYLI HS0904; MICROBIAL TRANSFORMATION; OPTIMIZATION OF PARAMETERS; OPTIMIZED CONDITIONS; PHYLOGENETIC ANALYSIS; PHYSIOLOGICAL CHARACTERISTICS; REACTION TEMPERATURE; RESTING CELLS; SHAKING SPEED; SOIL SAMPLE; SOLE CARBON SOURCE; SUBSTRATE CONCENTRATIONS; TRIFLUOROMETHYL; WHOLE CELL;

BACTERIOLOGY; ETHANOL; GLUCOSE; OPTIMIZATION; PH EFFECTS; SUBSTRATES;

KETONES;

3,5 BIS(TRIFLUOROMETHYL)ACETOPHENONE; [3,5 BIS(TRIFLUOROMETHYL)PHENYL]ETHANOL; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; BACTERIAL DNA; BUFFER; CARBONYL REDUCTASE; DNA 16S; GLUCOSE; UNCLASSIFIED DRUG;

ASYMMETRY; BACTERIUM; BIODEGRADATION; CATALYSIS; ENZYME ACTIVITY; ETHANOL; GENETIC ANALYSIS; IDENTIFICATION METHOD; KETONE; MORPHOLOGY; OPTIMIZATION; PHYLOGENETICS; REDUCTION; SOIL MICROORGANISM; SUBSTRATE;

ALCOHOL PRODUCTION; ARTICLE; BACTERIAL CELL; BACTERIAL STRAIN; BACTERIUM; BACTERIUM IDENTIFICATION; BACTERIUM ISOLATION; BACTERIUM TRANSFORMATION; BIOCATALYSIS; BIOCATALYST; BIOTRANSFORMATION; CARBON SOURCE; CONCENTRATION (PARAMETERS); DNA SEQUENCE; ENANTIOMER; ENZYME SUBSTRATE; LEIFSONIA XYLI; NONHUMAN; NUCLEOTIDE SEQUENCE; PH; PHYLOGENY; REACTION TIME; REDUCTION; SOIL MICROFLORA; STEREOSPECIFICITY; TEMPERATURE; VELOCITY; WHOLE CELL;

ACETOPHENONES; ACTINOMYCETALES; BACTERIAL TYPING TECHNIQUES; BENZYL ALCOHOLS; CLUSTER ANALYSIS; DNA, BACTERIAL; DNA, RIBOSOMAL; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PHYLOGENY; RNA, RIBOSOMAL, 16S; SEQUENCE ANALYSIS, DNA; SOIL MICROBIOLOGY;

BACTERIA (MICROORGANISMS); LEIFSONIA XYLI;

EID: 79958211247     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3233-3     Document Type: Article

References (23)

1. Bazhanov DP, Yatsevich KK, Bazhanova AA (2010) Phylogenetic identification of three strains of Rhizosphere bacteria based on the results of 16s rRNA gene analysis and genetic typing. Microbiology 79:374-384
2. 1 receptor antagonist aprepitant using a crystallization-induced diastereoselective transformation. J Am Chem Soc 125:2129-2135
3. Gelo-Pujic M, Guyader FL, Schlama T (2006) Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl] ethanone. Tetrahedron: Asymmetry 17:2000-2005 (Pubitemid 44205447)
4. II-bicp complexes. Angew Chem Int Ed 43:2816-2819
5. Hansen KB, Chilenski JR, Desmond R, Devine PN (2003) Scalable, efficient process for the synthesis of (R)-3,5-bistrifluoromethyl-phenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex. Tetrahedron: Asymmetry 14:3581-3587 (Pubitemid 37412482)
6. Homann MJ, Vail RB, Previte E, Tamarez M, Morgan B, Dodds DR, Zaks A (2004) Rapid identification of enantioselective ketone reductions using targeted microbial libraries. Tetrahedron 60:789-797 (Pubitemid 38045393)
7. Huisman GW, Liang J, Krebber A (2010) Practical chiral alcohol manufacture using ketoreductases. Curr Opin Chem Biol 14:122-129
8. Ju X, Yu HL, Pan J, Wei DZ, Xu JH (2010) Bioproduction of chiral mandelate by enantioselective deacylation of α-acetoxyphenylacetic acid using whole cells of newly isolated Pseudomonas sp. ECU1011. Appl Microbiol Biotechnol 86:83-91
9. Kaluzna IA, Rozzell JD, Kambourakis S (2005) Ketoreductases: stereoselective catalysts for the facile synthesis of chiral alcohols. Tetrahedron: Asymmetry 16:3682-3689 (Pubitemid 41681433)
10. Kumar S, Nei M, Dudley J, Tamura K (2008) MEGA: a biologist-centric software for evolutionary analysis of DNA and protein sequences. Brief Bioinformatics 9:299-306 (Pubitemid 351890826)
11. Kurbanoglu EB, Zilbeyaz K, Taskin M, Kurbanoglu NI (2009) Total production of (R)-3,5-bistrifluoromethylphenyl ethanol by a symmetric reduction of 3,5-bis(trifluoromethyl)-acetophenone in the submerged culture of Penicillium expansum isolate. Tetrahedron: Asymmetry 20:2759-2763
12. Kurbanoglu EB, Zilbeyaz K, Ozdal M, Taskin M, Kurbanoglu NI (2010) Asymmetric reduction of substituted acetophenones using once immobilized Rhodotorula glutinis cells. Bioresour Technol 101:3825-3829
13. Li W, Sun XF, Zhou L, Hou GH, Yu SC, Zhang XM (2009) Highly efficient and highly enantioselective asymmetric hydrogenation of ketones with tunesphos/1,2-diamine ruthenium(II) complexes. J Org Chem 74:1397-1399
14. Matsuda T, Yamanaka R, Nakamura K (2009) Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asymmetry 20:513-557
15. Pollard D, Truppo M, Pollard J, Chen CY, Moore J (2006) Effective synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol by asymmetric enzymatic reduction. Tetrahedron: Asymmetry 17:554-559
16. Susumu N, Tomoya O, Junsaku K (2008) Population pharmacokinetics of aprepitant and dexamethasone in the prevention of chemotherapy-induced nausea and vomiting. Cancer Chemother Pharmacol 63:75-83
17. Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0. Mol Biol Evol 24:1596-1599 (Pubitemid 47236692)
18. Thompson JD, Higgins DG, Gibson TJ (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680 (Pubitemid 24354800)
19. Vankawala PJ, Kolla N, Elati CR (2007) Efficient synthesis of (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a key intermediate for aprepitant, an NK-1 receptor antagonist. Synthetic Commun 37:3439-3446 (Pubitemid 47537119)
20. Wang P, Sun LM, He JY (2009) Medium optimization for enhanced production of carbonyl reductase by Candida tropicalis 104 by response surface methodology. Chin J Biotechnol 25:863-868
21. Wilson K (1997) Preparation of genomic DNA from bacteria. In: Ausubel FM, Kingston RE, Moore DD, Seidman JG, Smith JA, Struhl K (eds) Current protocols in molecular biology. Wiley, New York, pp 241-245
22. Xie Y, Xu JH, Xu Y (2010) Isolation of a Bacillus strain producing ketone reductase with high substrate tolerance. Bioresour Technol 101:1054-1059
23. Zerillo MM, Van Sluys MA, Camargo LE, Monteiro-Vitorello CB (2008) Characterization of new IS elements and studies of their dispersion in two subspecies of Leifsonia xyli. BMC Microbiol 8:127