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Master's Dissertation
Full name
Artur Franz Keppler
Knowledge Area
Date of Defense
São Paulo, 2005
Andrade, Leandro Helgueira de (President)
Di Vitta, Cláudio
Rodrigues, José Augusto Rosário
Title in Portuguese
Biotransformações de cetonas aromáticas e cíclicas promovidas por fungos
Keywords in Portuguese
Abstract in Portuguese
Nesse trabalho avaliamos o potencial enzimático de diferentes linhagens de fungos, visando determinar a presença de mono-oxigenases capazes de oxidar cetonas aromáticas e cíclicas. Todas as linhagens empregadas apresentaram atividade de álcool desidrogenase e Baeyer-Villiger mono-oxigenases. Adicionalmente foram sintetizadas oito moléculas bi-funcionalizadas com grupos sulfeto, seleneto e carbonila (cetona). Os produtos das reações biocatalisadas foram isolados e caracterizados.
Title in English
Biotransformations of cyclic and aromatic ketones by fungi
Keywords in English
Abstract in English
In this work, we evaluated the enzymatic potential of different Aspergillus strains, through the biotransformations of two substrates: 2- and 4-methylcyclohexanone (1a e 1b). All the strains employed showed alcohol dehydrogenase and Baeyer-Villiger monooxygenase (CPMO and CHMO) activities. These enzymes can perform ketone biorreduction and oxidation. Using the A. terreus SSP 1498 selected from the screening study, we prepared alcohols and lactones in good enantiosselectivity. In this way, other fungal strains were studied aiming to determine the presence of monooxygenase activity by means of the biotransformation of aromatic ketones. Like the Aspergillus, we observed that all strains used in this study showed alcohol dehydrogenase and Baeyer-Villiger monooxygenase (APMO) activities. We selected 1-phenyl-etanone and its para substituted derivates as substrates. Additionally, we synthesized eight examples of bi-functionalized compounds with sulfide, selenide and ketone groups. These compounds were submitted to the action of enzymatic system of different fungi which were selected from the initial screening. The products from the biotransformation were isolated and characterized.
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