High-performance liquid chromatographic enantioseparation of monoterpene-based 2-amino carboxylic acids on macrocyclic glycopeptide-based phases

László Sipos, István Ilisz, Zoltán Pataj, Zsolt Szakonyi, Ferenc Fülöp, Daniel W. Armstrong, Antal Péter

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The enantiomers of five monoterpene-based 2-amino carboxylic acids were directly separated on chiral stationary phases containing macrocyclic glycopeptide antibiotics such as teicoplanin (Astec Chirobiotic T and T2) and teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of pH, the mobile phase composition, the structure of the analyte and temperature on the separations were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 10-40°C to study the effects of temperature and thermodynamic parameters on separations. Apparent thermodynamic parameters and Tiso values were calculated from plots of lnk or lnα 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 enantioseparations were in most cases enthalpy driven. The sequence of elution of the enantiomers was determined in all cases.

Original languageEnglish
Pages (from-to)6956-6963
Number of pages8
JournalJournal of Chromatography A
Volume1217
Issue number44
DOIs
Publication statusPublished - Oct 29 2010

Keywords

  • Chirobiotic columns
  • Column liquid chromatography
  • Conformationally constrained
  • Macrocyclic glycopeptide-based chiral stationary phases
  • Monoterpene
  • β-Amino acid

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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