Biotransformation of alpha-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

Autor(es)

Rocha, Lenilson Coutinho ^[1] ; Ferreira, Hercules Vicente ^[1] ; Pimenta, Eli Fernando ^[1] ; Souza Berlinck, Roberto Gomes ^[1] ; Oliveira Rezende, Maria Olimpia ^[1] ; Landgraf, Maria Diva ^[1] ; Regali Seleghim, Mirna Helena ^[2] ; Sette, Lara Duraes ^[3] ; Meleiro Porto, Andre Luiz ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos, Dept Ecol & Biol Evolut, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Estadual Campinas, CPQBA, Recursos Div Microbianos, Ctr Pluridisciplinar Pesquisas Quim Biol Agr, BR-13140000 Paulinia, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: MARINE BIOTECHNOLOGY; v. 12, n. 5, p. 552-557, OCT 2010.
• Citações Web of Science: 34

Resumo

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. (AU)

• Processo FAPESP: 06/54401-2 - Biocatálise e biotransformação de compostos orgânicos com fungos marinhos, algas marinhas e reações catalisadas com enzimas comerciais
• Beneficiário: Andre Luiz Meleiro Porto
• Linha de fomento: Auxílio à Pesquisa - Regular