Enantiomeric separation of bicyclo[2.2.2]octane-based 2-amino-3-carboxylic acids on macrocyclic glycopeptide chiral stationary phases

Zoltán Pataj, István Ilisz, Nõra Grecsõ, Márta Palkõ, Ferenc Fülöp, Daniel W. Armstrong, Antal Péter

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Abstract

Direct high-performance liquid chromatographic (HPLC) separation of four bicyclo[2.2.2]octane based 2-amino-3-carboxylic acid enantiomers were developed on chiral stationary phases (CSPs) containing different macrocyclic glycopeptide antibiotic selectors. The analyses were performed under reversed-phase, polar organic and polar ionic mode on macrocyclic-glycopeptide-based Chirobiotic T, T2, TAG, and R columns. The effects of the mobile phase composition including the acid and base modifier, the structure of the analytes, and the temperature on the separations were investigated. Experiments were achieved at constant mobile phase compositions on different stationary phases in the temperature range 5-40C. Thermodynamic parameters were calculated from plots of ln k or ln α versus 1/T. It was recognized that the enantioseparations in reversed-phase and polar organic mode were enthalpically driven, but under polar-ionic conditions entropically driven enantioseparation was observed as well. Baseline separation and determination of elution sequence were achieved in all cases. Chirality 26:200-208, 2014. © 2014 Wiley Periodicals, Inc.

Original languageEnglish
Pages (from-to)200-208
Number of pages9
JournalChirality
Volume26
Issue number4
DOIs
Publication statusPublished - Apr 2014

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Keywords

  • column liquid chromatography
  • enantiomer separation
  • macrocyclic glycopeptide-based columns
  • β-amino acid analogs

ASJC Scopus subject areas

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

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