Enantioselective synthesis of optically active 2-oxazolidinones and alcohols catalysed by halohydrin dehalogenases

Mikleušević, Ana (2016) Enantioselective synthesis of optically active 2-oxazolidinones and alcohols catalysed by halohydrin dehalogenases. Doctoral thesis, Faculty of Science > Department of Chemistry.

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Abstract

A crude enzyme extracts of two halohydrin dehalogenases(HheC and HheA-N178A) for biocatalytic transformations with different substrates have been prepared. Racemic epoxides, oxazolidinones, azidoalcohols, cyanohydrins and bromoalcohols for substrates and/or standards for enzymatic reactions have been synthesized. Analytical methods of high performance liquid chromatography and gas chromatography on columns with chiral stationary phases for monitoring conversion, regio- and enantioselectivity of enzymatic reactions have been developed. Kinetic and dinamic kinetic resolution of racemic epibromohydrins in enzymatic reactions with different nucleophiles (cyanate, cyanide and azide) catalysed by halohydrin dehalogenase HheC have been studied. Catalytic activity of genetically modified halohydrin dehalogenase HheA-N178A in reactions of azidolysis of aromatic epoxides has been explored. As a result of this research, optically active 2-oxazolidinones and β-azidoalcohols have been prepared via biocatalytic reactions. A brighter insight in catalytic activity, regioselectivity and enantioselectivity of tested halohydrin dehalogenases has been given.

Item Type: Thesis (Doctoral thesis)
Keywords: dinamic kinetic resolution, epoxides, halohydrin-dehalogenases, kinetic resolution, oxazolidinones, β-azidoalcohols
Supervisor: Majerić Elenkov, Maja
Date: 2016
Number of Pages: 114
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Branka Maravic
Date Deposited: 11 May 2016 13:31
Last Modified: 11 May 2016 13:31
URI: http://digre.pmf.unizg.hr/id/eprint/4816

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