Enantioseparation of chiral fungicide enantiomers onpolysaccharide-based chiral columns

Author: marina karchkhadze
Co-authors: Lali Chankvetadze, Antonina Mskhiladze, Nino Kobakhidze, Bezhan Chankvetadze
Keywords: chiral fungicides, polysaccharide-based chiral selectors, separation of enantiomers
Annotation:

Fungicides are chemical compounds of pesticide’s group. These compounds destroy or prevent the development of pathological fungus; they also destroy some bacteria The classification of modern fungicides is based on the character of diseases they rae used agains for, their chemical nature and their affinity to water. The most of fungicides are chiral organic compounds of high physiological activity. Enantiomers of chiral fungicides differently act on plants. This makes necessary separation of fungicide enantiomers. Separation of the enantiomers of 10 chiral fungicides were studied on 4 cellulose- and 2 amylose-based chiral columns using polar-organic and aqueous-organic mobilephases.. The influence of the structure of polysaccharidal chiral selector and the composition of the mobile phase on separation of enantiomers was studied. The structure of chiral selector has significant impact on separation of enantiomers, in particular, as the structure of the main chain, as the nature and position of the substituents in aromatic ring. For example, penconazole enantiomers werecompletely separated on Cellulose-1 column and not separated on Amylose-1 column, although benzene ring of both selectors contain the same substituents in the same position;The enantiomers of penconazole were separated in methanol on Cellulose-2 column and not separated on Cellulose-4 column although benzene ring of both selectors contain the same substitutes but in differentposition. On Amylose-2 column, the enantiomers can’t be separated. The addition of 0.1% diethylamine and 5% water makes separation worse in case of triadimefone on Cellulose-1, Cellulose-2 and Cellulose-4 columns. The enantiomer elution order (EEO) depends on the nature of stationary phase. The EEOs of fenbuconazole enantiomers are opposite to each other on Cellulose-1 and Cellulose-3 columns, for Pencanazole – on Cellulose-1 and Cellulose-2 columns for every mobile phase used.

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ქიმიის დეპარტამენტის 2018 წლის სტუდენტთა სამეცნიერო წრის ანგარიში [ka]