Journal
JOURNAL OF CHROMATOGRAPHY A
Volume 1467, Issue -, Pages 169-177Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.chroma.2016.06.030
Keywords
Cationic cyclodextrin; Chiral stationary phase; High performance liquid chromatography; Click chemistry
Funding
- National Natural Science Foundation of China [21305066]
- Program for New Century Excellent Talents in University [NCET-12-0633]
- Natural Science Foundation for Distinguished Young Scholars of Jiangsu Province [BK20130032]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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In this work, a novel cationic cyclodextrin (CD) chiral stationary phase (CSPs) has been developed by clicking 6(A)-azido-6(C)-[(3-methoxylpropyI)-1- ammonium]-heptakis[2,3-di-O-(3-chloro-4-methylphenylcarbamate)-6(B),6(D),6(E),6(F),6(G)-pentakis-O-per(3-chloro-4-methylphenylcarbamate)-beta-CD chloride onto alkynyl silica support. The enantioselectivies of the as-obtained novel CSP were evaluated using 21 model racemates including flavonoids, aromatic alcohols, acidic drugs, beta-blocker and amino acids. Good enantioseparations were achieved in polar-organic phase high performance liquid chromatography (HPLC), with the highest resolution of 8.07 observed for 7-methoxyflavanone. The enantioseparations in normal-phase HPLC were fine-tuned with the polarity of the mobile phase with different alcohols as organic modifiers. Improved chiral resolutions of analytes but longer retention were observed in mobile phases with decreased polarity. On comparison with previously reported clicked CD CSP, the cationic CD clicked CSP exhibited better enenatioseparations for selected racemates even in normal-phase HPLC. The results indicate that 3-methoxypropylammonium and phenylcarbamoylated moieties of the cationic CSP may provide intermolecular interactions such as hydrogen bonding, pi-pi conjugation and dipole-dipole besides inclusion complexation to drive the enantioseparation. (C) 2016 Elsevier B.V. All rights reserved.
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