Redukcija prokiralnih ketona u prirodnim eutektičkim otapalima

master's thesis

• Title (english): Reduction of prochiral ketones in natural deep eutectic solvents
• Author: Anita Pušek
• Mentor: Marina Cvjetko Bubalo (mentor)
• Committee member: Ivana Radojčić Redovniković (predsjednik povjerenstva)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Biochemical Engineering); (Laboratory for Cell Technology, Application and Biotransformations); Zagreb
• Defense date and country: 2020-09-25, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U svrhu povećanja zelenog karaktera u biotransformacijskim postupcima proizvodnje biološki aktivnih spojeva, raste broj istraživanja usmjerenih na mogućnost primjene prirodnih eutektičkih otapala i enzima kao biokatalizatora, a čime se značajno smanjuje negativan učinak klasične kemijske sinteze. U ovom radu ispitan je utjecaj odabranih ekološki prihvatljivih eutektičkih otapala na bazi kolin-klorida i betaina na aktivnost i promjene u konformaciji enzima alkohol dehidrogenaze te na stabilnost reduciranog i oksidiranog oblika nikotinamidnog koenzima. Rezultati ispitivanja pokazali su da eutektička otapala betain:etilen-glikol i kolin-klorid:urea imaju stabilizirajući učinak na enzimsku aktivnost te na oba koenzima. Budući da su kiralni alkoholi ključni prekursori u dobivanju lijekova i finih kemikalija, u ovome radu je provedena reakcija enantioselektivne redukcije 2-kloro-1-(3,4-difluoro-fenil)etanona katalizirane oksidoreduktivnim enzimima pekarskog kvasca Saccharomyces cerevisiae u otapalu betain:etilen-glikol s različitim udjelima. Biokatalitička reakcija redukcije u eutektičkom otapalu betain:etilen-glikol rezultirala je većim iskorištenjem u odnosu na bioredukcije provedene u čistoj vodi i puferu.

Abstract (english)

For the purposes of increasing the green character in biotransformations for the production of biologically active compounds, the number of studies focused on the possibility of using natural eutectic solvents and enzymes as biocatalysts is growing, which significantly reduces the negative effect of classical chemical synthesis. In this study, the influence of selected environmentally friendly eutectic solvents based on choline chloride and betaine on the activity and changes in the conformation of the enzyme alcohol dehydrogenase and on the stability of the reduced and oxidized form of nicotinamide coenzyme was investigated. The test results showed that the eutectic solvents betaine: ethylene glycol and choline chloride: urea have a stabilizing effect on enzyme activity and on both coenzymes. Since chiral alcohols are the key precursors in the preparation of drugs and fine chemicals, the enantioselective reduction of 2-chloro-1- (3,4-difluoro-phenyl)ethanone catalyzed by oxidoreductive enzymes of the baker's yeast Saccharomyces cerevisiae in natural eutectic solvents betaine:ethylene-glycol with different water contents was performed. Additionally, the eutectic solvent choline-chloride: urea has also been shown as a suitable solvent in previous tests. The biocatalytic reduction reaction in the eutectic solvent betaine: ethylene glycol resulted in higher yields compared to the bioreductions performed in pure water and buffer.

• Keywords: alkohol dehidrogenaza; biokataliza; nikotinamidni koenzimi; prirodna eutektička otapala; redukcija; 2-kloro-1-(3; 4-difluorofenil)etanon
• Keywords (english): biocatalysis; natural eutectic solvents; reduction; 2-chloro-1- (3; 4-difluorophenyl)ethanone
• Language: croatian
• URN:NBN: urn:nbn:hr:159:693793
• Study programme: Title: Molecular Biotechnology; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka molekularne biotehnologije (magistar/magistra inženjer/inženjerka molekularne biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-12-16 14:35:41