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Bioconversion of Iodoacetophenones by Marine Fungi
Authors:Lenilson C Rocha  Rodrigo F Luiz  Isac G Rosset  Cristiano Raminelli  Mirna H R Seleghim  Lara Dur?es Sette  André L M Porto
Institution:Instituto de Química de S?o Carlos, Universidade de S?o Paulo, Av. Trabalhador, S?o-carlense, 400, CP 780, 13560-970, S?o Carlos, SP, Brazil.
Abstract:Nine marine fungi (Aspergillus sclerotiorum CBMAI 849, Aspergillus sydowii Ce19, Beauveria felina CBMAI 738, Mucor racemosus CBMAI 847, Penicillium citrinum CBMAI 1186, Penicillium miczynskii Ce16, P. miczynskii Gc5, Penicillium oxalicum CBMAI 1185, and Trichoderma sp. Gc1) catalyzed the asymmetric bioconversion of iodoacetophenones 1-3 to corresponding iodophenylethanols 6-8. All the marine fungi produced exclusively (S)-ortho-iodophenylethanol 6 and (S)-meta-iodophenylethanol 7 in accordance to the Prelog rule. B. felina CBMAI 738, P. miczynskii Gc5, P. oxalicum CBMAI 1185, and Trichoderma sp. Gc1 produced (R)-para-iodophenylethanol 8 as product anti-Prelog. The bioconversion of para-iodoacetophenone 3 with whole cells of P. oxalicum CBMAI 1185 showed competitive reduction-oxidation reactions.
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