High-performance liquid chromatographic chiral separation of β2-homoamino acids

Zoltán Pataj, Robert Berkecz, István Ilisz, Aleksandra Misicka, Dagmara Tymecka, Ferenc Fülöp, Daniel W. Armstrong, Antal Péter

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45°C and the changes in enthalpy, Δ(ΔH°) , entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The -Δ(ΔG°) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of β2-homoamino acids with branched alkyl or aryl side-chains, whereas for β2-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R < S.

Original languageEnglish
Pages (from-to)787-798
Number of pages12
JournalChirality
Volume21
Issue number9
DOIs
Publication statusPublished - Oct 1 2009

Keywords

  • B2-homoamino acids
  • Chirobiotic columns
  • Column liquid chromatography
  • Macrocyclic glycopeptide-based chiral stationary phases

ASJC Scopus subject areas

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

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