title: High-performance liquid chromatographic separation of unusual β(3)-amino acid enantiomers in different chromatographic modes on Cinchona alkaloid-based zwitterionic chiral stationary phases.
abstract: Polar-ionic and hydro-organic mobile phase mode of high-performance liquid chromatographic separations of 23 sterically constrained primary β(3)-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 β(3)-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.
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, 6720, Szeged, Hungary.
authors.forename: István
authors.initials: I
authors.lastname: Ilisz
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, 6720, Szeged, Hungary.|Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720, Szeged, Hungary.
authors.forename: Nóra
authors.initials: N
authors.lastname: Grecsó
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials, Palacký University, 17. listopadu 12, 771 46, Olomouc, Czech Republic.
authors.forename: Roman
authors.initials: R
authors.lastname: Papoušek
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, 6720, Szeged, Hungary.|Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials, Palacký University, 17. listopadu 12, 771 46, Olomouc, Czech Republic.
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Pataj
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials, Palacký University, 17. listopadu 12, 771 46, Olomouc, Czech Republic.
authors.forename: Petr
authors.initials: P
authors.lastname: Barták
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720, Szeged, Hungary.
authors.forename: László
authors.initials: L
authors.lastname: Lázár
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720, Szeged, Hungary.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.affiliation: Department of Analytical Chemistry, University of Vienna, Währingerstrasse 38, 1090, Vienna, Austria.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Lindner
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, 6720, Szeged, Hungary. apeter@chem.u-szeged.hu.
authors.forename: Antal
authors.initials: A
authors.lastname: Péter
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002930:Cinchona Alkaloids / Q000737:chemistry*; D008955:Models, Cardiovascular
chemical_list: D000596:Amino Acids; D002930:Cinchona Alkaloids
keywords: Cinchona alkaloid-based zwitterionic columns; Enantiomer separation; HPLC; β3-Amino acids