Estudos visando à síntese esterosseletiva da 4-ariltetralona e resolução cinética enzimática do 4-ariltetralol

• Main Author: Capeletto, Marina Gonçalves UNIFESP
• Other Authors: Craveiro, Graziela Gallego Bianco UNIFESP, Universidade Federal de São Paulo (UNIFESP)
• Format: Master Thesis
• Language: Portuguese
• Published: Universidade Federal de São Paulo 2014
• Subjects: Biorreduction; Enzymatic kinetic resolution; Aryltetralone; CaLB; DMC; Biorredução; Resolução cinética enzimática; Ariltetralona; Antarc*; Antarctica
• 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

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 ...