Enantioseparation of ketoprofen, ibuprofen and flurbiprofen on amylose tris(3-chloro-5-methylphenylcarbamate) chiral columns prepared by coating and covalent immobilization on the silica

Author: Gvantsa Sheklashvili
Co-authors: Mariam Maisuradze, Ana Chokheli
Keywords: Chromatography, Chiral selector, Enantiomers, Thermodynamic parameters, Isoenantioselective temperature, Elution order
Annotation:

The goal of the present thesis was to compare the enantioseparation of selected chiral arylpropionic acid derivatives on coated and immobilized columns, which have similar chiral selectors. Arylpropionic acid derivateves are widely used chiral drugs. They belong to non-steroidal anty-inflammatory drug group and are used as painkillers. Enantioseparation of chiral drugs is very important as their enantiomers commonly exhibit different pharmacological and toxicological properties. The chemical composition of the columns used in our experiments was the same. However, in case of Chiralpak IG and new immobilized column the polysaccharide derivative is covalently immobilized on silica, while on coated column the polysaccharide derivative is just physically adsorbted on silica. we compared thermodynamic parameters of conventionally coated and immobilized columns. Analysis were performed at different temperatures and in different mobile phases. For analyzed compounds the difference in adsorption enthalpy and adsorption entropy were calculated for enantiomers using the plot of natural logarithm of the separation factor versus the reciprocal of the absolute temperature. We calculated the thermodynamic parameters, which can help to predict the right conditions of the analysis for the given compound on a given column and to achieve the desired selectivity and elution order of enantiomers. By-changing the composition of mobile phases, we compared the stability and efficiency of coated and immobilized columns. The mobile phases studied were the mixture of n-hexane and polar organic component (2-propanol or ethanol) with the different volume ratio.

Lecture files:

კეტოპროფენის, იბუპროფენისა და ფლურბიპროფენის ენანტიომერების დაყოფის შესწავლა ამილოზა ტრის(3-ქლორ-5-მეთილფენილკარბამატის) დაფენით და კოვალენტური იმობილიზაციით მომზადებულ ქირალურ სვეტებზე [ka]