Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

Bo Yang; Jie Zhou; Yong Wang; Jian Tang; Weihua Tang

doi:10.1002/elps.201600491

Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

Electrophoresis. 2017 Aug;38(15):1939-1947. doi: 10.1002/elps.201600491. Epub 2017 Mar 16.

Authors

Bo Yang¹, Jie Zhou¹, Yong Wang², Jian Tang¹, Weihua Tang¹

Affiliations

¹ Key Laboratory of Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing, P. R. China.
² Department of Chemistry, School of Science, Tianjin University, Tianjin, P. R. China.

PMID: 28176345
DOI: 10.1002/elps.201600491

Abstract

The enantioseparations of 12 isoxazoline racemates were explored with four perphenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs) in high performance liquid chromatography (HPLC). The results demonstrated that the functionalities on phenylcarbamate moiety greatly determined the chiral separation ability of CD clicked CSPs. Among of them, per(3-chloro-4-methylphenylcarbamate) CD clicked CSP (CCC3M4-CSP) exhibited the best enantioseparation ability, affording 4ClPh-OPr with a chiral resolution over 20 in ternary eluent mobile phases. The optimization of CSPs structures provided wide platform for their chiral separations towards multi-mode HPLC.

Keywords: Chiral stationary phase; Enantioseparation; High performance liquid chromatography; Isoxazoline; Phenylcarbamate cyclodextrin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid / methods*
Cyclodextrins / chemistry*
Isoxazoles / analysis
Isoxazoles / chemistry*
Isoxazoles / isolation & purification*
Phenylcarbamates / chemistry*
Stereoisomerism

Substances

Cyclodextrins
Isoxazoles
Phenylcarbamates