Highly Enantioselective Production of R-Halohydrins with Whole Cells of Rhodotorula rubra KCh 82 CultureReportar como inadecuado




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





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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





Autor: Tomasz Janeczko * , Monika Dymarska and Edyta Kostrzewa-Susłow

Fuente: http://mdpi.com/



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