title: Biotransformation of α-bromoacetophenones by the marine fungus Aspergillus sydowii.
abstract: 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.
authors: Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador, São-carlense, 400, CEP 13560-970, CP 780, São Carlos, SP, Brazil.
authors: Lenilson Coutinho
authors: LC
authors: Rocha
authors: Hercules Vicente
authors: HV
authors: Ferreira
authors: Eli Fernando
authors: EF
authors: Pimenta
authors: Roberto Gomes Souza
authors: RG
authors: Berlinck
authors: Maria Olímpia Oliveira
authors: MO
authors: Rezende
authors: Maria Diva
authors: MD
authors: Landgraf
authors: Mirna Helena Regali
authors: MH
authors: Seleghim
authors: Lara Durães
authors: LD
authors: Sette
authors: André Luiz Meleiro
authors: AL
authors: Porto
mesh_terms: D000098:Acetophenones / Q000378:metabolism*; D001230:Aspergillus / Q000145:classification* / Q000378:metabolism*; D001711:Biotransformation / Q000502:physiology; D009792:Oceans and Seas; D013045:Species Specificity; D014871:Water Microbiology
chemical_list: D000098:Acetophenones; C013190:phenacyl bromide