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- Title
High-performance liquid chromatographic separation of unusual β-amino acid enantiomers in different chromatographic modes on Cinchona alkaloid-based zwitterionic chiral stationary phases.
- Authors
Ilisz, István; Grecsó, Nóra; Papoušek, Roman; Pataj, Zoltán; Barták, Petr; Lázár, László; Fülöp, Ferenc; Lindner, Wolfgang; Péter, Antal
- Abstract
Polar-ionic and hydro-organic mobile phase mode of high-performance liquid chromatographic separations of 23 sterically constrained primary β-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-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.
- Subjects
ENANTIOMERS; AMINO acid analysis; HIGH performance liquid chromatography; CINCHONA alkaloids; POLYZWITTERIONS; STATIONARY phase (Chromatography)
- Publication
Amino Acids, 2015, Vol 47, Issue 11, p2279
- ISSN
0939-4451
- Publication type
Article
- DOI
10.1007/s00726-015-2006-1