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. 2014 Dec 4;15(12):22392-404.
doi: 10.3390/ijms151222392.

Highly enantioselective production of (R)-halohydrins with whole cells of Rhodotorula rubra KCh 82 culture

Tomasz Janeczko  1 , Monika Dymarska  2 , Edyta Kostrzewa-Susłow  3
Affiliations

Highly enantioselective production of (R)-halohydrins with whole cells of Rhodotorula rubra KCh 82 culture

Tomasz Janeczko et al. Int J Mol Sci. .

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.

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Figures

Figure 1
Figure 1
Time dependence of transformation of: (A) 2-bromo-4'-chloroacetophenone (1c) and (B) 2,2',4'-trichloroacetophenone (1e) in the culture of Rhodotorula rubra KCh 82.
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