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

被引:0
作者
István Ilisz
Nóra Grecsó
Roman Papoušek
Zoltán Pataj
Petr Barták
László Lázár
Ferenc Fülöp
Wolfgang Lindner
Antal Péter
机构
[1] University of Szeged,Department of Inorganic and Analytical Chemistry
[2] University of Szeged,Institute of Pharmaceutical Chemistry
[3] Palacký University,Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials
[4] University of Vienna,Department of Analytical Chemistry
来源
Amino Acids | 2015年 / 47卷
关键词
Enantiomer separation; HPLC; β; -Amino acids; alkaloid-based zwitterionic columns;
D O I
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中图分类号
学科分类号
摘要
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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页码:2279 / 2291
页数:12
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