Enantioselective chromatography of β-aminoalcohols on polysaccharide based chiral stationary phases

Šporec, Anita (2015) Enantioselective chromatography of β-aminoalcohols on polysaccharide based chiral stationary phases. Doctoral thesis, Faculty of Science > Department of Chemistry.

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Abstract

Synthesis of twenty five model β-amino alcohols (β-aa) is described. Based on the synthetic approach applied for preparation, three classes of β-aa are identified: the first class is made by catalytic amonolysis of racemic derivatives of styrene oxide (43a-50a), the second by amonolysis of ethyl glycidyl ether (57-65) and the third by amonolysis of symmetric mesoepoxides(71-78). Prepared compounds were racemic mixtures of R- and S- enantiomers and efficient analytical methods for enantioseparation were developed using “chiral columns” connected with high performance liquid chromatograph and UV diode-array detector. For each combination of mobile phase composition and polysaccharide-based stationary phase, enantio-chromatographic parameters were studied (k1, Rs, α). For confirmation of enantiomerelution order (R- or S-) from the column, enantioenriched representative compounds were synthetized. Based on the enantioselective chromatography results mechanisms of chiral recognition of β-aa were proposed. Applicability of developed enantioselective methods was confirmed on four cardiovascular drugs with β-aa moiety: atenolol, sotalol, bisoprolol, carvedilol. It was found that the best enantioseparation of model β-amino alcohols and tested cardiovascular drugs was obtained with Chiralcel OD column.

Item Type: Thesis (Doctoral thesis)
Keywords: enantioselective chromatography, β-amino alcohols, polysaccharide-based stationary phases, cardiovascular drugs
Supervisor: Vinković, Vladimir
Date: 2015
Number of Pages: 205
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Zdenka Kuri
Date Deposited: 08 Sep 2015 12:07
Last Modified: 08 Sep 2015 12:07
URI: http://digre.pmf.unizg.hr/id/eprint/4225

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