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Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography.
Anal Chim Acta. 2012 Mar 09; 718:121-9.AC

Abstract

Two covalently bonded cationic β-CD chiral stationary phases (CSPs) prepared by graft polymerization of 6(A)-(3-vinylimidazolium)-6-deoxyperphenylcarbamate-β-cyclodextrin chloride or 6(A)-(N,N-allylmethylammonium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride onto silica gel were successfully applied in high-performance liquid chromatography (HPLC). Their enantioseparation capability was examined with 12 racemic pharmaceuticals and 6 carboxylic acids. The results indicated that imidazolium-containing β-CD CSP afforded more favorable enantioseparations than that containing ammonium moiety under normal-phase HPLC. The cationic moiety on β-CD CSPs could form strong hydrogen bonding with analytes in normal-phase liquid chromatography (NPLC) to enhance the analytes' retention and enantioseparations. In reversed-phase liquid chromatography (RPLC), the analytes exhibited their maximum retention when the pH of mobile phase was close to their pK(a) value. Inclusion complexation with CD cavity and columbic/ionic interactions with cationic substituent on the CD rim would afford accentuated retention and enantioseparations of the analytes.

Authors+Show Affiliations

Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, Singapore, Singapore.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

22305907

Citation

Wang, Ren-Qi, et al. "Cationic Cyclodextrins Chemically-bonded Chiral Stationary Phases for High-performance Liquid Chromatography." Analytica Chimica Acta, vol. 718, 2012, pp. 121-9.
Wang RQ, Ong TT, Tang W, et al. Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography. Anal Chim Acta. 2012;718:121-9.
Wang, R. Q., Ong, T. T., Tang, W., & Ng, S. C. (2012). Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography. Analytica Chimica Acta, 718, 121-9. https://doi.org/10.1016/j.aca.2011.12.063
Wang RQ, et al. Cationic Cyclodextrins Chemically-bonded Chiral Stationary Phases for High-performance Liquid Chromatography. Anal Chim Acta. 2012 Mar 9;718:121-9. PubMed PMID: 22305907.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography. AU - Wang,Ren-Qi, AU - Ong,Teng-Teng, AU - Tang,Weihua, AU - Ng,Siu-Choon, Y1 - 2012/01/08/ PY - 2011/10/19/received PY - 2011/12/13/revised PY - 2011/12/24/accepted PY - 2012/2/7/entrez PY - 2012/2/7/pubmed PY - 2012/5/23/medline SP - 121 EP - 9 JF - Analytica chimica acta JO - Anal Chim Acta VL - 718 N2 - Two covalently bonded cationic β-CD chiral stationary phases (CSPs) prepared by graft polymerization of 6(A)-(3-vinylimidazolium)-6-deoxyperphenylcarbamate-β-cyclodextrin chloride or 6(A)-(N,N-allylmethylammonium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride onto silica gel were successfully applied in high-performance liquid chromatography (HPLC). Their enantioseparation capability was examined with 12 racemic pharmaceuticals and 6 carboxylic acids. The results indicated that imidazolium-containing β-CD CSP afforded more favorable enantioseparations than that containing ammonium moiety under normal-phase HPLC. The cationic moiety on β-CD CSPs could form strong hydrogen bonding with analytes in normal-phase liquid chromatography (NPLC) to enhance the analytes' retention and enantioseparations. In reversed-phase liquid chromatography (RPLC), the analytes exhibited their maximum retention when the pH of mobile phase was close to their pK(a) value. Inclusion complexation with CD cavity and columbic/ionic interactions with cationic substituent on the CD rim would afford accentuated retention and enantioseparations of the analytes. SN - 1873-4324 UR - https://www.unboundmedicine.com/medline/citation/22305907/Cationic_cyclodextrins_chemically_bonded_chiral_stationary_phases_for_high_performance_liquid_chromatography_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0003-2670(12)00004-9 DB - PRIME DP - Unbound Medicine ER -