Methoxypropylamino β-cyclodextrin clicked AC regioisomer for enantioseparations in capillary electrophoresis

Jie Zhou; Yiying Wang; Yun Liu; Jian Tang; Weihua Tang

doi:10.1016/j.aca.2015.02.013

Methoxypropylamino β-cyclodextrin clicked AC regioisomer for enantioseparations in capillary electrophoresis

Anal Chim Acta. 2015 Apr 8:868:73-9. doi: 10.1016/j.aca.2015.02.013. Epub 2015 Feb 10.

Authors

Jie Zhou¹, Yiying Wang¹, Yun Liu¹, Jian Tang¹, Weihua Tang²

Affiliations

¹ College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.
² College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China. Electronic address: whtang@mail.njust.edu.cn.

PMID: 25813237
DOI: 10.1016/j.aca.2015.02.013

Abstract

In this work, a novel methoxypropylamino β-cyclodextrin (β-CD) clicked AC regioisomer, 6(A)-4-hydroxyethyl-1,2,3-triazolyl-6(C)-3-methoxypropylamino β-cyclodextrin (HETz-MPrAMCD), was synthesized via nucleophilic addition and click chemistry. The chiral separation ability of this AC regioisomer cationic CD was evaluated toward 7 ampholytic and 13 acidic racemates by capillary electrophoresis. Dependence of enantioselectivity and resolution on buffer pH (5.5-8.0) and chiral selector concentration (0.5-7.5 mM) was investigated. Enantioselectivities (α≥1.05) could be achieved for most analytes under optimal conditions except dansyl-DL-noreleucine and dansyl-DL-serine. The highest resolutions for 2-chloromandelic acid p-hydroxymandelic acid were 15.6 and 9.7 respectively. The inclusion complexation between HETz-MPrAMCD and each 3-phenyllactic acid enantiomer was also revealed with nuclear magnetic resonance study.

Keywords: AC regioisomer; Capillary electrophoresis; Cationic β-cyclodextrin; Chiral separations.