Avaliação do potencial biorredutor dos microrganismos isolados do processo de compostagem do Zoológico de São Paulo e resolução cinética enzimática do 1-tetralol em DMC e líquidos iônicos

• Main Author: Gutierres, Fernanda Camila 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 2015
• Subjects: Bioreduction; Enzymatic kinetic resolution; Acetophenone; Tetralol; DMC; Dicationic ionic liquids; Biorredução; Resolução cinética enzimática; Acetofenona; Líquidos iônicos dicatiônicos; Rugosa; Antarc*; Antarctica
• Online Access: http://repositorio.unifesp.br/handle/11600/46326; https://sucupira.capes.gov.br/sucupira/public/consultas/coleta/trabalhoConclusao/viewTrabalhoConclusao.jsf?popup=true&id_trabalho=2625753

The biocatalysis application in synthesis of natural products with biological activity has been an important tool in the organic chemistry. In this context, this academic master thesis involved two fronts: i)Bio-reduction screening of isolated microorganisms of the composting process of São Paulo zoo using the acetophenone as model compound and II) Enzymatic Kinetic Resolution of 1-tetralol (±)-3 in DMC and Ionic Liquids with isolated lipases. The first study front was related to the identification and evaluation of bio-reducer potential of the bacteria genus Bacillus sp (FPZSP678, FPZSP718, FPZSP737, TTIG726, TTIG727 and TTIG728) and Fungi from the soil of the Atlantic Forest (SP201, SP305, SP347, SP374 and SP345), which underwent bio-reduction reaction using acetophenone 1. In this study, the SP347 fungus strain, from the genus Mucor sp showed the best result in the conversion of 1 in TRIS buffer at pH 4,0, leading to 57% of phenyl-ethanol. The reactions were monitored in intervals of 24h for up to 168h, some reactions medium were evaluated as mineral culture medium, TRIS buffer at pH of 4,0 to 7,0; and sodium phosphate buffer with pH of 4,0 and 7,0. The second study path was related to Enzimatic Kinetic Resolution (RCE) of 1-tetralol (±)-3 with isolated lipases in dimethyl carbonate (DMC) and dicationic Ionic Liquids. Reactions using DMC as solvent were performed with the isolated lipases: Lipase from Candida rugosa (CrL), Amano Lipase of Pseudomonas fluorenscens (PfAL), Amano Lipase PS - immobilized on diatomite (PsAL) and Lipase of porcine pancreas (PpL). The reactions were carried for 12h at temperatures of 32 °C, 60 °C and 90 °C. The PsAL enzyme showed the best results of this series. (99% ee in 32 °C) Reactions using Ionic Liquids as solvent were performed with the lipase enzymes of Candida antarctica fraction B (CaLB), Amano Lipase of Pseudomonas fluorenscens (PfAL), and Amano Lipase of Pseudomonas cepacia. The reactions were performed at the temperatures of 32 °C, 60 °C and 90 °C in 3h using the ...