Asimetrična redukcija ketona pomoću natrijeva tetrahidroborata, kvasca S. cerevisiae i azuki graha

undergraduate thesis

• Title (english): Asymmetric reduction of a ketone by sodium tetrahydroborate, yeast S. cerevisiae and adzuki bean
• Author: Jelena Železnjak
• 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: 2012-07-25, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U ovom je radu provedena asimetrična redukcija 4-hidroksiacetofenona u 1-(4-hidorksifenil)etanol u vodi kao zelenom otapalu, pomoću kvasca Saccharomyces cerevisiae i azuki graha (Vigna angularis) 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 4-hidroksiacetofenona u 1-(4-hidroksifenil)etanol pomoću natrijeva tetrahidroborata klasičnom organskom sintezom u etanolu u prisutnosti β-ciklodekstrina. Struktura novosintetiziranog spoja 1-(4-hidroksifenil)etanola određena je IR-spektroskopijom, 1H- i 13C-nuklearnom magnetskom rezonancijom, a apsolutne konfiguracije kiralnog alkohola 1-(4-hidroksifenil)etanola određene su kiralnom HPLC.

Abstract (english)

In this paper novel asymmetric reduction of 4-hydroxyacetophenone into 1-(4-hydroxyphenyl)ethanol was carried out in water as green solvent by using baker's yeast S. cerevisiae and Adzuki bean (Vigna angularis) 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 4-hydroxyacetophenone into 1-(4-hydroxyphenyl)ethanol with sodium tetrahydroborate in ethanol in the presence of β-cyclodextrin was preformed, too. Structure of novel compound 1-(4-hydroxyphenyl)ethanol was determined by IR spectroscopy, 1H- and 13C-nuclear magnetic resonance, and absolute configurations of chiral alcohol 1-(4-hydroxyphenyl)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:159:518356
• Study programme: Title: Biotechnology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-05-16 09:01:36