Bioconversion of iodoacetophenones by marine fungi.
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.
Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador, São-carlense, 400, CP 780, 13560-970, São Carlos, SP, Brazil.
Lenilson C
LC
Rocha
Rodrigo F
RF
Luiz
Isac G
IG
Rosset
Cristiano
C
Raminelli
Mirna H R
MH
Seleghim
Lara Durães
LD
Sette
André L M
AL
Porto
D001230:Aspergillus / Q000145:classification / Q000378:metabolism*; D001711:Biotransformation; D017613:Iodine Compounds / Q000378:metabolism*; D007659:Ketones / Q000378:metabolism*; D009792:Oceans and Seas; D010407:Penicillium / Q000145:classification / Q000378:metabolism*; D013045:Species Specificity; D014242:Trichoderma / Q000145:classification / Q000378:metabolism*; D014871:Water Microbiology
D017613:Iodine Compounds; D007659:Ketones