High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids

Gyula Lajkó, Tímea Orosz, Nóra Grecsó, Beáta Fekete, Márta Palkó, F. Fülöp, Wolfgang Lindner, A. Péter, I. Ilisz

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Cyclic β-aminohydroxamic acid enantiomer pairs were stereoselectively separated by high-performance liquid chromatography on the recently developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+)™, ZWIX(-)™, ZWIX(+A) and ZWIX(-A). The results of variation of the applied chromatographic conditions, such as the bulk solvent composition, the concentrations and ratio of the acid and base additives, the presence of water as mobile phase additive and the counter-ion concentration furnished a better understanding of the retention mechanism. A thermodynamic study in the temperature range 5-50 °C revealed enthalpy-controlled enantiodiscrimination in all cases. The structure-selectivity relationships clearly indicated the importance of the strereochemistry of the functional groups. From an enantiorecognition aspect, the diexo position of the functional groups always proved more favorable than the diendo position. The elution sequence was determined in all cases and was found to reversed when ZWIX(+)™ was changed to ZWIX(-)™ or ZWIX(+A) to ZWIX(-A).

Original languageEnglish
Pages (from-to)84-94
Number of pages11
JournalAnalytica Chimica Acta
Volume921
DOIs
Publication statusPublished - May 19 2016

Fingerprint

Cinchona Alkaloids
alkaloid
Functional groups
functional group
liquid
Acids
Radiation counters
Enantiomers
acid
Base Composition
High performance liquid chromatography
Liquids
enthalpy
Thermodynamics
liquid chromatography
Enthalpy
thermodynamics
High Pressure Liquid Chromatography
Ions
Temperature

Keywords

  • Chiral zwitterionic ion-exchangers
  • Direct chiral separations
  • Enantiomers of cyclic β-aminohydroxamic acids
  • HPLC
  • Temperature dependence of chiral separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Environmental Chemistry
  • Biochemistry
  • Spectroscopy

Cite this

High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids. / Lajkó, Gyula; Orosz, Tímea; Grecsó, Nóra; Fekete, Beáta; Palkó, Márta; Fülöp, F.; Lindner, Wolfgang; Péter, A.; Ilisz, I.

In: Analytica Chimica Acta, Vol. 921, 19.05.2016, p. 84-94.

Research output: Contribution to journalArticle

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AU - Orosz, Tímea

AU - Grecsó, Nóra

AU - Fekete, Beáta

AU - Palkó, Márta

AU - Fülöp, F.

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