High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids

I. Ilisz, Zsanett Gecse, Gyula Lajkõ, E. Forró, F. Fülöp, Wolfgang Lindner, A. Péter

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, the nature and concentrations of the acid and base additives, the counterions and temperature on the separations were investigated. The changes in standard enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated from the linear van't Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10-50°C). The values of the thermodynamic parameters depended on the nature of the selectors and the structures of the analytes. Unusual temperature behavior was observed on the ZWIX(-) column: decreased retention times were accompanied by increased separation factors with increasing temperature. On the ZWIX(+) column only enthalpically, whereas on the ZWIX(-) column both enthalpically and entropically driven separations were observed. The elution sequence was determined in all cases and was observed to be the opposite on ZWIX(+) and on ZWIX(-). Chirality 27:563-570, 2015.

Original languageEnglish
Pages (from-to)563-570
Number of pages8
JournalChirality
Volume27
Issue number9
DOIs
Publication statusPublished - Sep 1 2015

Fingerprint

Cyclic Amino Acids
Cinchona Alkaloids
Amino acids
Temperature
Liquids
Enantiomers
Chirality
Entropy
Thermodynamics
Phase composition
Free energy
Enthalpy
Acids

Keywords

  • Cinchona alkaloid-based chiral stationary phases
  • cyclic β-amino acids
  • enantiomer separation
  • HPLC

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids. / Ilisz, I.; Gecse, Zsanett; Lajkõ, Gyula; Forró, E.; Fülöp, F.; Lindner, Wolfgang; Péter, A.

In: Chirality, Vol. 27, No. 9, 01.09.2015, p. 563-570.

Research output: Contribution to journalArticle

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