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Evaluation of synergistic enantioseparation systems with chiral spirocyclic ionic liquids as additives by capillary electrophoresis

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Abstract

In recent years, chiral ionic liquids (CILs) have attracted more and more attention in the field of enantioseparation. In this study, two novel spirocyclic chiral ionic liquids, 1-butyl-3-methylimidazolium(T-4)-bis[(2S)-2-(hydroxy-κO)-3-methylbutanoato-κO]borate (BMIm+BLHvB−) and 1-butyl-3-methylimidazolium (T-4)-bis[(αS)-α-(hydroxy-κO)-4-methylbenzeneacetato-κO]borate (BMIm+BSMB−), were applied for the first time in capillary electrophoresis (CE) to establish synergistic systems for enantiomeric separation. Significantly improved separations of five tested analytes were observed in the CILs synergistic systems based on three β-cyclodextrin derivatives (CD), compared with conventional single CD separation systems. Several principal parameters such as CILs concentration, cyclodextrin concentration, buffer pH, and applied voltage were systematically investigated with BMIm+BLHvB−/hydroxypropyl-β-CD selected as a model system to optimize the enantioseparation. Molecular modeling was applied to further demonstrate the chiral recognition mechanism of the CILs/hydroxypropyl-β-CD synergistic system, which showed a good agreement with the experimental results.

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Acknowledgments

This work was supported by the Project of National Natural Science Foundation of China (Nos. 81373378 and 81072610), the Natural Science Foundation of Jiangsu Province (Program No. BK20150697) and the Project of the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

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Authors and Affiliations

  1. Department of Analytical Chemistry, China Pharmaceutical University, Nanjing, 210009, Jiangsu, China

    Yanjie Zhang, Zijie Feng, Yingxiang Du & Zhi Yan

  2. College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China

    Shuaijing Du

  3. Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, 210009, Jiangsu, China

    Yingxiang Du

  4. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, Jiangsu, China

    Yingxiang Du

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  1. Yanjie Zhang
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Correspondence to Yingxiang Du.

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Zhang, Y., Du, S., Feng, Z. et al. Evaluation of synergistic enantioseparation systems with chiral spirocyclic ionic liquids as additives by capillary electrophoresis. Anal Bioanal Chem 408, 2543–2555 (2016). https://doi.org/10.1007/s00216-016-9356-8

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  • DOI: https://doi.org/10.1007/s00216-016-9356-8

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