"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography

Y Wang; David James Young; T T Y Tan; S C Ng

doi:10.1016/j.chroma.2010.10.059

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"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography

Journal article

Peer reviewed

"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography

Y Wang, David James Young, T T Y Tan and S C Ng

Journal of Chromatography A, Vol.1217(50), pp.7878-7883

2010

DOI: https://doi.org/10.1016/j.chroma.2010.10.059

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Abstract

"Click" chemistry

cyclodextrin

chiral stationay phases

HPLC

This communication reports the preparation of two new cyclodextrin (CD) chiral stationary phases (CSPs): heptakis(6-deoxy-6-azido)-β-CD and heptakis(6-deoxy-6-azido-phenylcarbamoylated)-β-CD CSPs that perform quite differently to our previously reported " click" immobilized CD-CSPs. These CSPs are sterically congested at the narrow mouth of the CD and exhibit chiral discrimination between over 40 pairs of enantiomers in high performance liquid chromatography. The free hydroxyl CSP afforded better separation of indoprofen, ketoprofen, Tröger's base, hydroxyl, carboxylic and dansyl amino acids than did the phenylcarbamoylated CSP, while the latter was better at resolving aryl alcohols, flavonoids, β-blockers and β-agonists. The current work shows that enantiodiscrimination achieved with different CSPs for different classes of analyte may be correlated with CD accessibility and peripheral functionality. © 2010 Elsevier B.V.

Details

Title: "Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography
Authors: Y Wang (Author) - Nanyang Technological University, Singapore
David James Young (Author) - Universiti Brunei Darussalam, Brunei
T T Y Tan (Author) - Nanyang Technological University, Singapore
S C Ng (Author) - Nanyang Technological University, Singapore
Publication details: Journal of Chromatography A, Vol.1217(50), pp.7878-7883
Publisher: Elsevier BV
Date published: 2010
DOI: 10.1016/j.chroma.2010.10.059
ISSN: 0021-9673
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449259702621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Biochemical Research Methods; Chemistry, Analytical