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Int. J. Mol. Sci. 2014, 15(12), 22392-22404; doi:10.3390/ijms151222392

Highly Enantioselective Production of (R)-Halohydrins with Whole Cells of Rhodotorula rubra KCh 82 Culture

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
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Received: 13 October 2014 / Revised: 24 November 2014 / Accepted: 25 November 2014 / Published: 4 December 2014
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Abstract

Biotransformation of ten α-haloacetophenones in the growing culture of the strain Rhodotorula rubra KCh 82 has been carried out. Nine of the substrates underwent an effective enantioselective reduction to the respective (R)-alcohols according to Prelog’s rule, with the exception of 2-chloro-1,2-diphenylethan-1-one that was not transformed by this strain. The expected reduction proceeded without dehalogenation, leading to the respective (R)-halohydrins in high yields. The use of this biocatalyst yielded (R)-2-bromo-1-phenyl-ethan-1-ol (enantiomeric excess (ee) = 97%) and its derivatives: 4'-Bromo- (ee = 99%); 4'-Chloro- (ee > 99%); 4'-Methoxy- (ee = 96%); 3'-Methoxy- (ee = 93%); 2'-Methoxy- (ee = 98%). There were also obtained and characterized 2,4'-dichloro-, 2,2',4'-trichloro- and 2-chloro-4'-fluoro-phenyetan-1-ol with >99% of enantiomeric excesses. View Full-Text
Keywords: enantiospecific reduction; β2-adrenoceptor-stimulating agent; (R)-halohydrins; Rhodotorula rubra enantiospecific reduction; β2-adrenoceptor-stimulating agent; (R)-halohydrins; Rhodotorula rubra
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Janeczko, T.; Dymarska, M.; Kostrzewa-Susłow, E. Highly Enantioselective Production of (R)-Halohydrins with Whole Cells of Rhodotorula rubra KCh 82 Culture. Int. J. Mol. Sci. 2014, 15, 22392-22404.

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