Comparison of the separation performances of cinchona alkaloid-based zwitterionic stationary phases in the enantioseparation of β2- And β3-amino acids

István Ilisz, Nóra Grecsó, Aleksandra Misicka, Dagmara Tymecka, László Lázár, Wolfgang Lindner, Antal Péter

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The enantiomers of twelve unusual β2- and β3-homoamino acids containing the same side-chains were separated on chiral stationary phases containing a quinine- or quinidine-based zwitterionic ion-exchanger as chiral selector. The effects of the mobile phase composition, the nature and concentration of the acid and base additives and temperature on the separations were investigated. The changes in standard enthalpy, Δ(ΔH° ), entropy, Δ(ΔS° ), and free energy, Δ(ΔG° ), were calculated from the linear van't Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10-50 °C). The values of the thermodynamic parameters depended on the nature of the selectors, the structures of the analytes, and the positions of the substituents on the analytes. A comparison of the zwitterionic stationary phases revealed that the quinidine-based ZWIX(-)™ column exhibited much better selectivity for both β2- and β 3-amino acids than the quinine-based ZWIX(+)™ column, and the separation performances of both the ZWIX(+)™ and ZWIX(-)™ columns were better for β2-amino acids. The elution sequence was determined in some cases and was observed to be R < S and S < R on the ZWIX(+)™ and ZWIX(-)™ columns, respectively.

Original languageEnglish
Pages (from-to)70-87
Number of pages18
JournalMolecules
Volume20
Issue number1
DOIs
Publication statusPublished - Jan 1 2015

Keywords

  • Cinchona alkaloid-based chiral stationary phases
  • Column liquid chromatography
  • β-amino acids
  • β-amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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