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High-performance liquid chromatographic separation of unusual β3-amino acid enantiomers in different chromatographic modes on Cinchona alkaloid-based zwitterionic chiral stationary phases

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Abstract

Polar-ionic and hydro-organic mobile phase mode of high-performance liquid chromatographic separations of 23 sterically constrained primary β3-amino acid enantiomers containing, alkyl, aryl or heteroaryl side-chains were carried out by using newly developed Cinchona alkaloid-based zwitterionic chiral selectors and the stationary phases Chiralpak ZWIX(+)™ and ZWIX(−)™. In the polar-ionic mode, the effects of the composition of the bulk solvent and the natures of the co- and counter-ions, while in the hydro-organic mode, the effects of the pH, the counter-ion concentration and the structures of the analytes were investigated. The separations of the enantiomers of these 23 primary β3-amino acids, which can be classified as a series of quasi- (pseudo-) homologs, were optimized in both chromatographic modes. The elution sequence was determined in most cases and a reversal of elution order on ZWIX(+)™ and ZWIX(−)™ column was observed. On the basis of this intermolecular recognition model between the selectors and the given enantiomers an indirect assignment of the resolved enantiomer via chromatography is proposed.

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Acknowledgments

This work was supported by Hungarian National Science Foundation grant OTKA K 108847. AP gratefully acknowledges the support of Pilar Franco (Chiral Technologies Europe) for the Chiralpak columns. RP, PZ and PB gratefully acknowledge the support of the Ministry of Education, Youth and Sports of the Czech Republic (NPU LO 1305), Operational Program “Education for Competitiveness” (CZ.1.07/2.3.00/30.0041), and Palacký University in Olomouc (IGA_PrF_2014031).

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The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, 6720, Szeged, Hungary

    István Ilisz, Nóra Grecsó, Zoltán Pataj & Antal Péter

  2. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720, Szeged, Hungary

    Nóra Grecsó, László Lázár & Ferenc Fülöp

  3. Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials, Palacký University, 17. listopadu 12, 771 46, Olomouc, Czech Republic

    Roman Papoušek, Zoltán Pataj & Petr Barták

  4. Department of Analytical Chemistry, University of Vienna, Währingerstrasse 38, 1090, Vienna, Austria

    Wolfgang Lindner

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  1. István Ilisz
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  2. Nóra Grecsó
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  3. Roman Papoušek
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Correspondence to Antal Péter.

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Ilisz, I., Grecsó, N., Papoušek, R. et al. High-performance liquid chromatographic separation of unusual β3-amino acid enantiomers in different chromatographic modes on Cinchona alkaloid-based zwitterionic chiral stationary phases. Amino Acids 47, 2279–2291 (2015). https://doi.org/10.1007/s00726-015-2006-1

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