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

Janeczko, Tomasz; Dymarska, Monika; Kostrzewa-Susłow, Edyta

doi:10.3390/ijms151222392

Volume 15, Issue 12

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

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

Tomasz Janeczko *

, Monika Dymarska

and Edyta Kostrzewa-Susłow

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland

Author to whom correspondence should be addressed.

Received: 13 October 2014 / Revised: 24 November 2014 / Accepted: 25 November 2014 / Published: 4 December 2014

(This article belongs to the Section Biochemistry)

Full-Text | PDF [840 KB, uploaded 4 December 2014] |

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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

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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.