Recent studies on chiral recognition and enantioseparations in liquid phase

Author: Bezhan Chankvetadze
Co-authors: I. Matarashvili, L. Mosiashvili, L. Chankvetadze, S. Samakashvili, M. Karchkhadze, A. Mskhiladze, B. Chankvetadze
Annotation:

This presentation summarizes our recent სტუდიეს in the field of enantioseparation using polysaccharide-based chiral columns in high-performance liquid chromatography (HPLC). In particular, the reversal of enantiomer elution order of chiral analytes depending on composition, nature and concentration of minor additives of the mobile phase, as well as unusual increase of the retention and separation selectivity with increasing analysis temperature will be discussed. Novel series of polysaccharide-based chiral stationary phases (CSP) were used for HPLC separation of enantiomers under normal-phase and polar organic mobile phase conditions [1-3]. In capillary electrophoresis opposite affinity of the enantiomers of ketoprofen was observed to permethylated cyclodextrins and the possible structural mechanisms of this phenomenon studied with nuclear magnetic resonance spectroscopy [4]. Chiral analytes studied involved arylpropionic acid derivatives [1, 4], -blockers [2], imidazole and triazole derivatives [3], some of them with multiple centers of chirality. Possible mechanisms of observed phenomena will be discussed. In addition chiral HPLC was used for studying of novel catalysts for green enantioselective synthesis [5, 6] and for following a biological activity and enantioselective transformation and accumulation of chiral agrochemical difenoconazole in environment [7]. References: 1. I. Matarashvili, S. Fanali, L. Chankvetadze, T. Farkas, B. Chankvetadze, J. Sep. Sci., 36 2013, 140-147. 2. L. Mosiashvili, L. Chankvetadze, T. Farkas, B. Chankvetadze, J. Chromatogr. A 1317, 2013, 167-174. 3. A. Mskhiladze, M. Karchkhadze, A. Dadianidze, S. Fanali, T. Farkas, B. Chankvetadze, Chromatographia, 76, 2013, 1449-1458. 4. S. Samakashvili, A. Salgado, G. Scriba, B. Chankvetadze, Chirality, 25, 2013, 79–88. 5. A. Pinaka, G. C. Vougioukalakis, D. Dimotikali, E. Yannakopoulou, B. Chankvetadze, K. Papadopoulos, Chirality, 25, 2013, 119-125. 6. A. Pinaka, D. Dimotikali, B. Chankvetadze, K. Papadopoulos, G.C. Vougioukalakis, Synlett, 24, 2013, 2401-2446. 7. F. Dong, J. Li, B. Chankvetadze, Y. Cheng, X. Liu, J. Xu, X. Chen, Y. Li, C. Bertucci, D. Tedesco, R. Zanasi, Y. Zheng, Environ. Sci. & Tech., 47, 2013, 3386-3394.