Citation: WU Zhi-Hua, ZHAO Jie, LI Shen, WANG Yong. Enantioseparation Performance Tuning of Novel Cyclodextrin Chiral Separation Materials via Click Chemistry[J]. Chinese Journal of Analytical Chemistry, ;2016, 44(1): 95-102. doi: 10.11895/j.issn.0253-3820.150611 shu

Enantioseparation Performance Tuning of Novel Cyclodextrin Chiral Separation Materials via Click Chemistry

WU Zhi-Hua ¹ ,
ZHAO Jie ² ,
LI Shen ¹ ,
WANG Yong ^1,3,,

1.
¹ Department of Chemistry, School of Science Tianjin University, Tianjin 300072, China;
2.
² Institute of Agricultural Resource and Environment Tianjin Academy of Agricultural Science, Tianjin 300192, China;
3.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China

Corresponding author: WANG Yong,
Received Date: 31 July 2015
Available Online: 13 November 2015
Fund Project: 本文系国家自然科学基金(No.21205086) (No.21205086)天津市自然科学基金(No.13JCQNJC05400) (No.13JCQNJC05400)天津大学自主创新基金(No.2015XRX-0021)资助项目 (No.2015XRX-0021)

This work fabricates four novel chiral stationary phases (CSPs) by tuning the functionality on cyclodextrin (CD) small mouth via click chemistry. Mono-6-deoxy-azido CD was anchored onto silica surface via ether linkage, followed by introducing tert-butyl, phenyl, ester and hydroxyl groups to the azido CD silica respectively. The as-prepared four novel CD CSPs were characterized by FTIR and elemental analysis. 16 enantiomer pairs including isoxazolines and dansyl amino acids could be baseline or partially separated on the current CD CSPs under reversed-phase separation mode. Ester functionalized CD CSP exhibited good chiral recognition towards isoxazolines and the resolution of 2-chlorphenyl-isoxazole(2ClPh-OPr)reached 1.62. The optimum pH for the separation of dansyl amino acids was 5.0. Among the prepared CSPs, Tert-butyl functionalized CD CSP had the best enantioseparation performance towards dansyl amino acids with most of the analytes baseline separated (R_s>1.5).
- High performance liquid chromatography,
- Cyclodextrin,
- Chiral stationary phase,
- Click chemistry
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