Direct high-performance liquid chromatographic separation of unusual secondary amino acids and a comparison of the performances of Chirobiotic T and TAG columns

Antal Péter, Roland Török, Daniel W. Armstrong

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30 Citations (Scopus)

Abstract

Two macrocyclic glycopeptide antibiotic-type chiral stationary phases (CSPs) based on native teicoplanin and teicoplanin aglycone, Chirobiotic T and TAG, respectively, were evaluated with regard to the high-performance liquid chromatographic separation of the enantiomers of 10 secondary α-amino acids (imino acids). The chromatographic results are given as the retention, separation and resolution factors, together with the enantioselective free energy difference corresponding to the separation of the enantiomers. By application of these two CSPs, excellent resolutions were achieved for the investigated compounds by using reversed-phase mobile mode systems. The separation conditions were optimized by variation of the mobile phase composition. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP for these particular amino acids ranged between 0.70 and -1.83 kJ mol -1. It was established that better enantioseparations of the secondary α-amino acids were attained in most cases on the aglycone CSP.

Original languageEnglish
Pages (from-to)229-235
Number of pages7
JournalJournal of Chromatography A
Volume1057
Issue number1-2
DOIs
Publication statusPublished - Nov 19 2004

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Keywords

  • Chirobiotic T and TAG
  • Direct enantiomeric separation
  • High-performance liquid chromatography
  • Macrocyclic antibiotic-type stationary phases
  • Secondary amino acids ("imino acids")

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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