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Biotransformation of alpha-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

By Lenilson Coutinho ROCHA, Hercules Vicente FERREIRA, Eli Fernando PIMENTA, Roberto Gomes Souza BERLINCK, Maria Olimpia Oliveira REZENDE, Maria Diva LANDGRAF, Mirna Helena Regali SELEGHIM, Lara Duraes SETTE and Andre Luiz Meleiro PORTO

Abstract

The biotransformation reactions of alpha-bromoacetophenone (1), p-bromo-alpha-bromoacetophenone (2), and p-nitro-alpha-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 alpha-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 alpha-chloroacetophenone 5 (9%) and alpha-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

Topics: Marine fungus, Aspergillus sydowii, alpha-Bromoacetophenone, Biotransformation, MEDIATED ASYMMETRIC REDUCTION, CHIRAL CATALYTIC SOURCE, BAKERS-YEAST REDUCTION, MICROBIAL REDUCTION, PROCHIRAL KETONES, HYDRIDE TRANSFER, HALOACETOPHENONES, MICROORGANISMS, Biotechnology & Applied Microbiology, Marine & Freshwater Biology
Publisher: SPRINGER
Year: 2013
OAI identifier: oai:agregador.ibict.br.RI_UNICAMP:oai:unicamp.sibi.usp.br:SBURI/1158
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