Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol
This academic Master involved two different and complementary paths of work: i) the study of biorreduction of 4-aryltetralone (±)-5 and bio-oxidation of 4-aryltetralol (±)-6 with microorganisms; ii) study of Enzymatic Kinetic Resolution (EKR) of (±)-6 with isolated lipases. The first path of work wa...
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Universidade Federal de São Paulo
2014
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Online Access: | http://repositorio.unifesp.br/handle/11600/46328 https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=1361155 |
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ftunivfsaopaulo:oai:repositorio.unifesp.br:11600/46328 2023-10-09T21:46:29+02:00 Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol Capeletto, Marina Gonçalves UNIFESP Craveiro, Graziela Gallego Bianco UNIFESP Universidade Federal de São Paulo (UNIFESP) 2014-06-06 199 p. application/pdf http://repositorio.unifesp.br/handle/11600/46328 https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=1361155 por por Universidade Federal de São Paulo https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=1361155 CAPELETTO, Marina Goncalves. Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol. 2014. 199 f. Dissertação (Mestrado) - Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo (UNIFESP), Diadema, 2014. http://repositorio.unifesp.br/handle/11600/46328 2014-0083.pdf Acesso restrito Biorreduction Enzymatic kinetic resolution Aryltetralone CaLB DMC Biorredução Resolução cinética enzimática Ariltetralona Dissertação de mestrado 2014 ftunivfsaopaulo 2023-09-17T15:10:58Z This academic Master involved two different and complementary paths of work: i) the study of biorreduction of 4-aryltetralone (±)-5 and bio-oxidation of 4-aryltetralol (±)-6 with microorganisms; ii) study of Enzymatic Kinetic Resolution (EKR) of (±)-6 with isolated lipases. The first path of work was related to the study and evaluation of biocatalysis, using microorganisms of the Fungi Kingdom (yeasts and molds) as bioreductors and bio-oxidants in the aryltetralone’s resolution. These studies were conducted using phosphate buffer, the microorganism growth medium and two-phase systems. Among the microorganisms studied, the Rhodotorula mucilaginosa proved to be the best yeast for both bioreduction of 4-aryltetralone as for bio-oxidation of 4-aryltetralol. The best results were obtained in the bio-oxidation, which combined with the EKR of (±)-6 lead to (R)-4-aryltetralone 5 in 73% ee. The other path of work was related to the EKR of 4-aryltetralol (±)-6 using isolated lipases in different solvents. We looked for environmentally friendly solvents, with less toxicity, less pollutants characteristics and less volatile, such as dimethyl carbonate (DMC), 2-methyltetrahydrofuran and cyclopentyl methyl ether. In order to find the best reaction condition, we used the Candida antarctica Lipase - fraction B (CaLB) as biocatalyst. After, the optimized condition was applied to other lipases. The results showed that several solvents can be used in the EKR of aryltetralol (±)-6 mainly the environmentally acceptable ones, highlighting the DMC, which lead to the complete resolution of (±)-6 in 3 h. The CaLB showed, among lipases studied, the best catalyst for EKR of aryltetralol. Furthermore, the results of EKR contributed to the characterization of aryltetralol (±)-6 and acetate (±)-7 isomers. Este mestrado acadêmico envolveu duas frentes de trabalho: i) o estudo de biorredução da 4-ariltetralona (±)-5 e bio-oxidação do 4-ariltetralol (±)-6 com microrganismos; ii) estudo de Resolução Cinética Enzimática (RCE) do 4-ariltetralol ... Master Thesis Antarc* Antarctica Universidade Federal de São Paulo (UNIFESP): Repositório Institucional |
institution |
Open Polar |
collection |
Universidade Federal de São Paulo (UNIFESP): Repositório Institucional |
op_collection_id |
ftunivfsaopaulo |
language |
Portuguese |
topic |
Biorreduction Enzymatic kinetic resolution Aryltetralone CaLB DMC Biorredução Resolução cinética enzimática Ariltetralona |
spellingShingle |
Biorreduction Enzymatic kinetic resolution Aryltetralone CaLB DMC Biorredução Resolução cinética enzimática Ariltetralona Capeletto, Marina Gonçalves UNIFESP Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
topic_facet |
Biorreduction Enzymatic kinetic resolution Aryltetralone CaLB DMC Biorredução Resolução cinética enzimática Ariltetralona |
description |
This academic Master involved two different and complementary paths of work: i) the study of biorreduction of 4-aryltetralone (±)-5 and bio-oxidation of 4-aryltetralol (±)-6 with microorganisms; ii) study of Enzymatic Kinetic Resolution (EKR) of (±)-6 with isolated lipases. The first path of work was related to the study and evaluation of biocatalysis, using microorganisms of the Fungi Kingdom (yeasts and molds) as bioreductors and bio-oxidants in the aryltetralone’s resolution. These studies were conducted using phosphate buffer, the microorganism growth medium and two-phase systems. Among the microorganisms studied, the Rhodotorula mucilaginosa proved to be the best yeast for both bioreduction of 4-aryltetralone as for bio-oxidation of 4-aryltetralol. The best results were obtained in the bio-oxidation, which combined with the EKR of (±)-6 lead to (R)-4-aryltetralone 5 in 73% ee. The other path of work was related to the EKR of 4-aryltetralol (±)-6 using isolated lipases in different solvents. We looked for environmentally friendly solvents, with less toxicity, less pollutants characteristics and less volatile, such as dimethyl carbonate (DMC), 2-methyltetrahydrofuran and cyclopentyl methyl ether. In order to find the best reaction condition, we used the Candida antarctica Lipase - fraction B (CaLB) as biocatalyst. After, the optimized condition was applied to other lipases. The results showed that several solvents can be used in the EKR of aryltetralol (±)-6 mainly the environmentally acceptable ones, highlighting the DMC, which lead to the complete resolution of (±)-6 in 3 h. The CaLB showed, among lipases studied, the best catalyst for EKR of aryltetralol. Furthermore, the results of EKR contributed to the characterization of aryltetralol (±)-6 and acetate (±)-7 isomers. Este mestrado acadêmico envolveu duas frentes de trabalho: i) o estudo de biorredução da 4-ariltetralona (±)-5 e bio-oxidação do 4-ariltetralol (±)-6 com microrganismos; ii) estudo de Resolução Cinética Enzimática (RCE) do 4-ariltetralol ... |
author2 |
Craveiro, Graziela Gallego Bianco UNIFESP Universidade Federal de São Paulo (UNIFESP) |
format |
Master Thesis |
author |
Capeletto, Marina Gonçalves UNIFESP |
author_facet |
Capeletto, Marina Gonçalves UNIFESP |
author_sort |
Capeletto, Marina Gonçalves UNIFESP |
title |
Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
title_short |
Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
title_full |
Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
title_fullStr |
Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
title_full_unstemmed |
Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
title_sort |
estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol |
publisher |
Universidade Federal de São Paulo |
publishDate |
2014 |
url |
http://repositorio.unifesp.br/handle/11600/46328 https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=1361155 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=1361155 CAPELETTO, Marina Goncalves. Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol. 2014. 199 f. Dissertação (Mestrado) - Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo (UNIFESP), Diadema, 2014. http://repositorio.unifesp.br/handle/11600/46328 2014-0083.pdf |
op_rights |
Acesso restrito |
_version_ |
1779322193352589312 |