High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases

László Sipos, István Ilisz, Melinda Nonn, Ferenc Fülöp, Zoltán Pataj, Daniel W. Armstrong, Antal Péter

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Abstract

The enantiomers of four unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids were directly separated on chiral stationary phases containing macrocyclic glycopeptide antibiotics teicoplanin (Astec Chirobiotic T and T2), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V) and vancomycin aglycone (Chirobiotic VAG) as chiral selectors. The effects of the mobile phase composition, the structure of the analytes and temperature on the separations were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 5-45 °C to study the effects of temperature, and thermodynamic parameters were calculated from plots of ln. k or ln α versus 1/ T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpy-driven. The sequence of elution of the enantiomers was determined in all cases.

Original languageEnglish
Pages (from-to)142-151
Number of pages10
JournalJournal of Chromatography A
Volume1232
DOIs
Publication statusPublished - Apr 6 2012

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Keywords

  • Chirobiotic columns
  • Column liquid chromatography
  • Isoxazoline-fused 2-aminocyclopentanecarboxylic acids
  • Macrocyclic glycopeptide-based chiral stationary phases

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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