Application of Insoluble Cellulose 3,5-Dichlorophenylcarbamate Attached to the Surface of Silica for Separation of Enantiomers in High-Performance Liquid Chromatography

Author: Eka Tsutskiridze
Keywords: Chirality, Enantiomers, Chromatography
Annotation:

Separation of enantiomers belongs to one of the hot topics in contemporary chemistry. The importance of this topic is warranted by the fact that individual enantiomers of chiral drugs may exhibit different bioactivities and toxicities. Only in 1980s chiral columns for high-performance liquid chromatographic (HPLC) separation of enantiomers became commercially available. Among all chiral stationary phases (CSP) available today for HPLC separation of enantiomers, these based on polysaccharide derivatives are considered to be the most useful materials. Polysaccharide-based CSPs are commonly prepared by physical coating of polysaccharide derivative onto the surface of silica. The coated-type polysaccharide-based CSPs are not compatible with organic solvents dissolving the chiral selector and thus, damaging the column. In order to overcome this drawback the current trend is to immobilize or make insoluble the polysaccharide derivative onto the surface of silica. The major research goal of our job is evaluating the enantiomer resolving ability of the new chiral columns made on the basis of insoluble cellulose 3,5-dichlorophenylcarbamate. The results of this study will further extend the applicability of polysaccharide-based CSPs for liquid phase separation of enantiomers, as well as help in better understanding of chiral recognition mechanisms with these materials. We have studied the enantiomer resolving ability of the new chiral columns made on the basis of insoluble cellulose 3,5-dichlorophenylcarbamate with conventional Methanol, Acetonitrile and aqueous-organic mobile phases, as well as in combination with atypical mobile phase tert-butyl methylether (C5H12O). The results were compared with the enantiomer resolving ability of coated columns in the appropriate conditions. The column was evaluated for separation of enantiomers of various groups of chiral drugs such as arylpropionic acid derivatives, beta-blockers, dihydropyridine derivatives, antimycotics of diazole and triazole groups, etc. Results of experiment showed that using of Immobilized and coated chiral columns have revealed same results. Though, the immobilized columns has an advantage, we can use it for separation of enantiomers, when we have used strong mobile phase, such as tert-butyl methyl ether (C5H12O).