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Enantioseparation using carboxymethyl-6-(4-methoxybenzylamino)-β-cyclodextrin as a chiral selector by capillary electrophoresis and molecular modeling study of the recognition mechanism

Authors :
Yu Zhao
Xingjie Guo
Jinlong Wang
Yanru Liu
Yongbo Song
Zhen Jiang
Source :
New Journal of Chemistry. 44:958-972
Publication Year :
2020
Publisher :
Royal Society of Chemistry (RSC), 2020.

Abstract

In this study, carboxymethyl-6-(4-methoxybenzylamino)-β-cyclodextrin (CMCDPN) was synthesized for the first time and managed to be used as a chiral selector to enantioseparate 13 kinds of chiral drugs (chlorpheniramine, brompheniramine, pheniramine, homatropine, homatropine methyl, clorprenaline, terbutaline, procaterol, tulobuterol, cycloclenbuterol, propranolol, pindolol and ofloxacin) by capillary electrophoresis (CE). The analysis was carried out by CE using a fused-silica capillary (50 cm × 50 μm i.d., 40 cm effective length) with 30 mmol L−1 phosphate buffer under an applied voltage of 20 kV. The effect of analysis conditions such as buffer concentration, buffer pH, applied voltage and concentration of the chiral selector on the enantioseparation results was systematically investigated. By the method established by us, eleven of the analytes reached baseline separation and the other two reached partial separation. The molecular dockings were applied to further demonstrate the mechanisms of chiral recognition. The docking results showed good agreement with our experimental results.

Details

ISSN :
13699261 and 11440546
Volume :
44
Database :
OpenAIRE
Journal :
New Journal of Chemistry
Accession number :
edsair.doi...........f812ba659f60efb34641ac1e0b4b3130