Article ID Journal Published Year Pages File Type
1163476 Analytica Chimica Acta 2015 7 Pages PDF
Abstract

In this paper, we demonstrate:•The click synthesis of a AC regioisomer cationic cyclodextrin (CD) as chiral selector.•The good enantioselectivities (chiral resolution over 5) for acidic racemates.•The strong chiral recognition of new CD by NMR study.•Baseline enantioseparation of some acidic racemates at CD of 0.5 mM.

In this work, a novel methoxypropylamino β-cyclodextrin (β-CD) clicked AC regioisomer, 6A-4-hydroxyethyl-1,2,3-triazolyl-6C-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.

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Physical Sciences and Engineering Chemistry Analytical Chemistry
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