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