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

Yong Wang, David James Young, Timothy Thatt Yang Tan, Siu Choon Ng

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)7878-7883
Number of pages6
JournalJournal of Chromatography A
Volume1217
Issue number50
DOIs
Publication statusPublished - 10 Dec 2010
Externally publishedYes

Fingerprint

Cyclodextrins
High performance liquid chromatography
High Pressure Liquid Chromatography
Hydroxyl Radical
Indoprofen
Ketoprofen
Enantiomers
Flavonoids
Mouth
Alcohols
Amino Acids
Communication

Cite this

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title = "{"} Click{"} preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography",
abstract = "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, Tr{\"o}ger'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.",
keywords = "{"} Click{"} chemistry, Chiral stationay phases, Cyclodextrin, HPLC",
author = "Yong Wang and Young, {David James} and Tan, {Timothy Thatt Yang} and Ng, {Siu Choon}",
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language = "English",
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" Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography. / Wang, Yong; Young, David James; Tan, Timothy Thatt Yang; Ng, Siu Choon.

In: Journal of Chromatography A, Vol. 1217, No. 50, 10.12.2010, p. 7878-7883.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - " Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography

AU - Wang, Yong

AU - Young, David James

AU - Tan, Timothy Thatt Yang

AU - Ng, Siu Choon

PY - 2010/12/10

Y1 - 2010/12/10

N2 - 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.

AB - 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.

KW - " Click" chemistry

KW - Chiral stationay phases

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KW - HPLC

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