Issue 15, 2015

“One-pot” click access to triazole bridged cyclodextrin chiral phases for differentiation of clopidogrel enantiomers

Abstract

The current work demonstrates a “one-pot” click synthetic procedure for the preparation of triazole bridged cyclodextrin (CD) chiral stationary phases (CSPs) and their application for efficient chiral differentiation of clopidogrel enantiomers under reversed-phase high performance liquid chromatography (HPLC). It was found that native-CD-CSPs and methylated-CD-CSPs showed good enantioselectivity towards clopidogrel enantiomers with acetonitrile (ACN)/water and methanol (MeOH)/water as mobile phases, respectively, while the more versatile phenylcarbamoylated-CD-CSP cannot resolve the enantiomers due to the steric hindrance of bulky phenylcarbamate moieties. Solvent selection plays an important role in CSP chiral recognition ability towards clopidogrel enantiomers. 6-Hydroxyl moieties on CD rims were found to participate in the chiral recognition process. The optimal chiral resolution (Rs) was improved to 1.95 by transferring the separation from 5 μm native-CD-CSPs to 3 μm native-CD-CSPs with ACN/buffer as the mobile phase.

Graphical abstract: “One-pot” click access to triazole bridged cyclodextrin chiral phases for differentiation of clopidogrel enantiomers

Supplementary files

Article information

Article type
Paper
Submitted
27 May 2015
Accepted
01 Jul 2015
First published
02 Jul 2015

Anal. Methods, 2015,7, 6432-6436

Author version available

“One-pot” click access to triazole bridged cyclodextrin chiral phases for differentiation of clopidogrel enantiomers

Q. Kang, X. Yao, L. Zhang, Z. Wu and Y. Wang, Anal. Methods, 2015, 7, 6432 DOI: 10.1039/C5AY01365H

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