Asimetrična redukcija 3,4-dimetilacetofenona pomoću NaBH4 i bioloških katalizatora

master's thesis

• Title (english): Asymmetric reduction of 3,4-dimethylacetophenone by NaBH4 and biocatalysts
• Author: Ana Potočki
• Mentor: Jasna Vorkapić-Furač (mentor)
• 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: 2012-09-25, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U ovom je radu provedena asimetrična redukcija 3,4-dimetil acetofenona u 1-(3,4dimetilfenil)etanol u vodi kao zelenom otapalu uz mikrovalnu aktivaciju, pomoću kvasca Saccharomyces cerevisiae i dijelova različitih biljaka (graha, slanutka i leće) kao zelenim biokatalizatorima. Navedeni biokatalizatori su pomoću svojih enzima izveli asimetričnu redukciju supstrata, čime se pokazala njihova povoljna uporaba u biotransformacijama prema principima zelene kemije. Radi usporedbe enantioselektivnosti, izvedena je redukcija 3,4dimetilacetofenona u 1-(3,4-dimetilfenil)etanol pomoću natrijeva tetrahidroborata klasičnom organskom sintezom u etanolu u prisutnosti β-ciklodekstrina. Struktura sintetiziranog spoja 1-(3,4-dimetilfenil)etanola određena je IR-spektroskopijom, 1H- i 13C-nuklearnom magnetskom rezonancijom, a apsolutne konfiguracije kiralnog alkohola 1-(3,4dimetilfenil)etanola određene su kiralnom HPLC.

Abstract (english)

In this paper novel asymmetric reduction of 3,4-dimethylacetophenone into 1-(3,4dimetphenyl)ethanol was carried out in water as green solvent using microwave activation, by using baker's yeast S. cerevisiae and parts of plants (beans, chick pea and lentil) as green biocatalysts. The enzymes of these biocatalysts preformed the asymmetric reduction of a substrate, showing why they are good for using in biotransformations according to the principles of green chemistry. For comparison of enantioselectivity, the reduction of 3,4dimethylacetophenone into 1-(3,4-dimethylphenyl)ethanol with sodium tetrahydroborate in ethanol in the presence of β-cyclodextrin was preformed, too. Structure of compound 1-(3,4dimethylyphenyl)ethanol was determined by IR spectroscopy, 1H- and 13C-nuclear magnetic resonance, and absolute configurations of chiral alcohol 1-(3,4-dimethylphenyl)ethanol by chiral HPLC.

• Keywords: asimetrična redukcija; biljke; biotransformacije; kvasac; zelena kemija
• Keywords (english): asymmetric reduction; baker's yeast; biotransformation; green chemistry; plants
• Language: croatian
• URN:NBN: urn:nbn:hr:159:933748
• Study programme: Title: Bioprocess Engineering; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka bioprocesnog inženjerstva (magistar/magistra inženjer/inženjerka bioprocesnog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-05-09 08:44:41