შოთა რუსთაველის საქართველოს ეროვნული სამეცნიერო ფონდი

Shota Rustaveli National Science Foundation of Georgia

For Science, for Future, for Georgia

საქართველოს განათლებისა და მეცნიერების სამინისტრო
GE

Successful projects and scientists

Synthesis of chiral sulphoxides and hydantoins, separation of their enantiomers in high-performance liquid chromatography and study of molecular mechanisms of enantioseparations

The project N04/22: Synthesis of chiral sulphoxides and hydantoins, separation of their enantiomers in high-performance liquid chromatography and study of molecular mechanisms of enantioseparations, has been revealed as winner project in 2015 joint call of the Shota Rustaveli National Science Foundation of Georgia (RNSF) and the National Research Council (CNR), Italy. Coordinator of the project is Bezhan Chankvetadze, Full Professor of Ivane Javakhishvili Tbilisi State University, academician of the Georgian National Academy of Sciences. The main aim of the project was synthesis of novel chiral sulfoxides and hydantoins and study of enantioselective recognition mechanisms using polysaccharide-based chiral selectors in high-performance liquid chromatography.

Enantiomers are the molecules with the same structural formula but different spatial arrangement of atoms, so that a pair of enantiomers represents nonsuperimposable mirror-images of one another. They are known as optical isomers. Enantiomers of a given chiral compound exhibit different biological activity – pharmacokinetics, pharmacodynamics and toxicity. As a rule, in racemic drug, just one enantiomer is biologically active, while the other may cause unwanted side effects, or even toxic effects. Removing of the unwanted enantiomer from the racemic drug significantly increases drug efficacy and safety. The problem is that the resolution of enantiomers is very complicated process due to almost the same physical and chemical properties of enantiomers. Nowadays more than half of synthetic drugs exist as racemic mixture with 50:50 % ratio of enantiomers.

In the frame of the present project, in order to investigate relationships between enantioselectivity and structure of chiral compound / chiral selector, about 50 new chiral sulfoxides and hydantoins were synthesized by our research group. Their enantiomeric resolution was studied by high-performance liquid chromatographic method using chiral stationary phases. The relationships between the structure of analyte, stationary and mobile phases and enantioselectivity were revealed.

Research results were represented at many international and national conferences. Two papers were published and several papers are in preparation for publishing in highly ranked international journals.

  • G. D´Orazio, R. Kakava, A. Volonterio, S. Fanali, B. Chankvetadze, An attempt for fast separation of enantiomers in nano-liquid chromatography and capillary electrochromatography, Electrophoresis, 2017; 38(15):1932-1938
  • C. West, M.-L. Konjaria, N. Shashviashvili, E. Lemasson, P. Bonnet, R. Kakava, A. Volonterio, B.  Chankvetadze, Enantioseparation of novel chiral sulfoxides on chlorinated polysaccharide stationary phases in supercritical fluid chromatography, J. Chromatogr. A 1499, 2017, 174-182.