High-performance liquid chromatographic enantioseparation of β2-amino acids using a long-tethered (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase

István Ilisz, Zoltán Pataj, Róbert Berkecz, Aleksandra Misicka, Dagmara Tymecka, Ferenc Fülöp, Hee Jung Choi, Myung Ho Hyun, Antal Péter

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19 Citations (Scopus)

Abstract

Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-amino acids on a new chiral stationary phase, using the 11-methylene-unit spacer of aminoundecylsilica gel for the bonding of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as selector. The nature and concentration of the acidic and organic modifiers, the pH, the mobile phase composition, and the structures of the analytes substantially influenced the retention and resolution. Separations were carried out at constant mobile phase compositions in the temperature range 7-40 °C and the changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and free energy, Δ(ΔG°) were calculated. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers.

Original languageEnglish
Pages (from-to)1075-1082
Number of pages8
JournalJournal of Chromatography A
Volume1217
Issue number7
DOIs
Publication statusPublished - Feb 12 2010

Keywords

  • Column liquid chromatography
  • Long-tethered (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase
  • Spacer length effect
  • Temperature effect
  • β-Amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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