Plant-mediated asymmetric reduction of 1-(3, 4-dimethylphenyl) ethanone (CROSBI ID 239956)
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Podaci o odgovornosti
Pavoković, Dubravko ; Buđa, Renata ; Andrašec, Fran ; Roje, Marin ; Cvjetko Bubalo, Marina ; Radojčić Redovniković, Ivana
engleski
Plant-mediated asymmetric reduction of 1-(3, 4-dimethylphenyl) ethanone
Bioreduction mediated by plants is a highly selective and environmentally friendly approach to synthesise optically active alcohols. Herein the bioreduction of 1-(3, 4)- dimethylphenyl)ethanone to the corresponding chiral alcohol 1- (3, 4-dimethylphenyl)ethanol has been evaluated using nine different vegetables roots as biocatalysts. The chiral alcohol was prepared in yields ranging from 44.1% to 88.2%, and with enantiomeric excess up to 97.2% for the (S)-enantiomer. Sugar beet was the most promising among the tested vegetables roots. Therefore, sugar beet cell cultures (normal and transformed) were obtained and tested for the reduction as well, yielding the corresponding alcohol in the range from 62.1% to 88.2% yield and with enantiomeric excesses of >99%. Based on these results reported, there are no profound differences in the reductive capacity of undifferentiated cells and organs of the same plant species (sugar beet). Due to overall advantages of using cell cultures, we have highlighted this approach as a promising method for preparation of enantiomerically pure 1-(3, 4- dimethylphenyl)ethanol.
Bioreduction, 1-(3, 4)-dimethylphenyl)ethanone, chiral alcohols, biocatalysis, vegetable roots
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