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Mémoire de Maîtrise
DOI
https://doi.org/10.11606/D.75.2009.tde-13112009-144835
Document
Auteur
Nom complet
Ana Maria Mouad
Adresse Mail
Unité de l'USP
Domain de Connaissance
Date de Soutenance
Editeur
São Carlos, 2009
Directeur
Jury
Porto, Andre Luiz Meleiro (Président)
Debonsi, Hosana Maria
Sette, Lara Durães
Titre en portugais
Biocatalisadores de origem marinha (algas, bactérias e fungos) para redução estereosseletiva de cetonas
Mots-clés en portugais
Bostrychia radicans
Bostrychia tenella
Algas Marinhas
Cetonas
Fungos Marinhos
Redução
Resumé en portugais
Neste trabalho foram realizadas reações de redução de cetonas empregando diferentes organismos marinhos como biocatalisadores (algas, fungos e bactérias). Nas triagens foram utilizados derivados de acetofenonas (o-iodoacetofenona, m-iodoacetofenona, p-iodoacetofenona, o-fluoracetofenona, o-cloroacetofenona, o-bromoacetofenona, o-nitroacetofenona) e duas cetonas 1,3-dicarboniladas: a 4,4,4-triflúor-1-(furan-2-il)butano-1,3-diona e a 4,4,4-triflúor-1-(naftalen-2-il)butano-1,3-diona. As reações com as algas marinhas Bostrychia tenella e a Bostrychia radicans levaram aos álcoois com excelentes seletividades (ee >98%), contudo, obtiveram-se baixas conversões. Foram isoladas as bactérias Bt-01 (B. tenella) e Bt-02 (B. radicans), as quais catalisaram as reduções das acetofenonas com resultados similares aos obtidos com as algas. Os fungos (Br-09, Br-23, Br-27, Br-61) isolados da alga B. radicans reduziram as acetofenonas com boas seletividades e conversões. Ainda, reações de redução das acetofenonas com quatro linhagens de fungos isolados da alga Sargassum sp (SMA2-C, SMA2-8, SMA2-58, SGPY-41) levaram a obtenção dos respectivos álcoois com diferentes conversões e seletividades. As reduções das cetonas 1,3-dicarboniladas foram realizadas com as algas B. tenella e B. radicans, e com sete linhagens de fungos marinhos (Aspergillus sydowii Ce15, Aspergillus sydowii Ce19, Aspergillus sydowii Gc12, Bionectria sp Ce5, Penicillium raistrickii Ce16, Penicillium miczynskii Gc5 e Trichoderma sp Gc1). As algas e os fungos marinhos catalisaram a redução regiosseletiva e estereosseletiva das cetonas 1,3-dicarboniladas, onde ocorreu a redução do grupo α-trifluorcarbonílico. Concluiu-se que as algas e seus microrganismos associados, e os fungos marinhos têm potencial para serem utilizados como biocatalisadores em reações de redução. Este trabalho foi o primeiro estudo realizado no país envolvendo algas marinhas e seus microrganismos associados em reações de redução de cetonas, cujos resultados são bastante promissores.
Titre en anglais
Biocatalysts from marine origin (algae, bacteria and fungi) for stereoselectivy reduction of ketones
Mots-clés en anglais
Bostrychia radicans
Bostrychia tenella
Algae marine
Ketones
Marine fungi
Reduction
Resumé en anglais
In this work, were investigated the ketone reduction reactions using several marine organisms as biocatalysts (algae, fungi and bacteria). In the screening were utilized acetophenone derivatives (o-iodoacetophenone, m-iodoacetophenone, p-iodoacetophenone, o-fluoroacetophenone, o-chloroacetophenone, o-bromoacetophenone, o-nitroacetophenone) and two 1,3-dicarbonylated compounds: 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione and 4,4,4-trifluoro-1-(naftalen-2-yl)butane-1,3-dione. The reactions with algae Bostrychia tenella and Bostrychia radicans afforded the alcohols with high selectivities (ee > 98%), however, with low conversions. The bacteria Bt-01 and Bt-02 were isolated from algae B. tenella and B. radicans, respectively, which catalyzed the reductions of acetophenones as the same as obtained with the algae. The acetophenones were reduced by several fungi (Br-09, Br-23, Br-27, Br-61) in good selectivities and conversions. These fungi were isolated from Bostrychia radicans. In addition, the acetophenone reduction reactions were screened with four strains of fungi, which were isolated from algae Sargassum sp (SMA2-C, SMA2-8, SMA2-58, SGPY-41). The alcohols were obtained with different conversions and selectivities. The reductions of 1,3-dicarbonylated compounds were carried out with the algae B. tenella and B. radicans, and marine fungi (Aspergillus sydowii Ce15, Aspergillus sydowii Ce19, Aspergillus sydowii Gc12, Bionectria sp Ce5, Penicillium raistrickii Ce16, Penicillium miczynskii Gc5 and Trichoderma sp Gc1). The algae and marine fungi catalyzed regio- and estereoselectively reductions of the 1,3-dicarbonylated compounds. The α-trifluoromethylcarbonyl group was reduced preferentially. In conclusion, the algae and associated micro-organisms and marine fungi have potential for catalyzing ketone reduction reactions. This investigation was the first study carried out in the Brazil by using algae and associated micro-organisms in the ketone reduction reactions. The obtained results here are promising and interesting.
 
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Date de Publication
2010-06-29
 
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