Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Alcohols Q 0230Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-phenylethanols. -The enantioselective bioreduction of α-substituted acetophenones (I), (III), (V), and (VII) is studied using various cells of fungi. The alcohol production at various fungal biomass concentrations is also investigated. The chiral alcohols obtained by this methodology are important intermediates for asymmetric syntheses of drugs. -(ANDRADE*, L. H.; POLAK, R.; PORTO, A. L. M.; SCHOENLEIN-CRUSIUS, I. H.; COMASSETO, J. V.; Lett. Org. Chem. 3 (2006) 8, 613-618; Lab. Quim. Fina Biocatal., Inst. Quim., Univ. Sao Paulo, 05508 Sao Paulo, Brazil; Eng.) -M. Bohle

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Biotransformation of α-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

Rocha

Ferreira

Pimenta

et al. 2009

Mar Biotechnol

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The biotransformation reactions of α-bromoacetophenone (1), p-bromo-α-bromoacetophenone (2), and p-nitro-α-bromoacetophenone (3) by whole cells of the marine fungus Aspergillus sydowii Ce19 have been investigated. Fungal cells that had been grown in artificial sea water medium containing a high concentration of chloride ions (1.20 M) catalysed the biotransformation of 1 to 2-bromo-1-phenylethanol 4 (56%), together with the α-chlorohydrin 7 (9%), 1-phenylethan-1,2-diol 9 (26%), acetophenone 10 (4%) and phenylethanol 11 (5%) identified by GC-MS analysis. In addition, it was observed that the enzymatic reaction was accompanied by the spontaneous debromination of 1 to yield α-chloroacetophenone 5 (9%) and α-hydroxyacetophenone 6 (18%) identified by GC-FID analysis. When 2 and 3 were employed as substrates, various biotransformation products were detected but the formation of halohydrins was not observed. It is concluded that marine fungus A. sydowii Ce19 presents potential for the biotransformations of bromoacetophenone derivatives.

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Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha-Substituted-1-Phenylethanols

Cited by 11 publications

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Bioreduction by Microorganisms

Bioreduction by Microorganisms

Application of Bioreduction by Microorganisms in the Enantioselective Synthesis of Alpha‐Substituted‐1‐phenylethanols.

Biotransformation of α-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

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