LC enantioseparation of aryl-substituted β-lactams using variable-temperature conditions

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Abstract

Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of β-lactams. The enantiomers of 7 aryl-substituted β-lactams were separated on chiral stationary phases containing the macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T) and teicoplanin aglycone (Chirobiotic TAG) at 10-°C increments in the range 5-45°C, using different compositions of 0.1% aqueous triethylammonium acetate (pH 4.1)/methanol (v/v) as mobile phase. The mobile phase composition and temperature were varied to achieve baseline resolutions in a single chromatographic run. The dependence of the natural logarithms of the selectivity factors ln α on the inverse of temperature, 1/T, was used to determine the thermodynamic data on the enantiomers. The thermodynamic data revealed that all the compounds in this study undergo separation via the same enthalpy-driven chiral recognition mechanism. The different methods were compared in systematic chromatographic examinations. The effects of the organic modifier, the mobile phase composition and the temperature on the separation were investigated.

Original languageEnglish
Pages (from-to)S29-S35
JournalChromatographia
Volume63
Issue numberSUPPL. 13
DOIs
Publication statusPublished - Jun 1 2006

Keywords

  • Chirobiotic T and TAG columns
  • Column liquid chromatography
  • Temperature effect
  • β-Lactams

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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