Structural and temperature effects on enantiomer separations of bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids on cinchona alkaloid-based zwitterionic chiral stationary phases

I. Ilisz, Nóra Grecsó, Márta Palkó, F. Fülöp, Wolfgang Lindner, A. Péter

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Procedures for the direct high-performance liquid chromatographic enantiomer separation of four bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids were developed in polar-ionic mode on zwitterionic chiral stationary phases (CSPs) based on cinchonane alkaloide quinine, quinidine and chiral sulfonic acid motifs. The effects of the mobile phase composition including the type of acid and base additives, the structures of the analytes and temperature were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 10-50. °C in order to study the effects of temperature, and thermodynamic parameters were calculated from plots of ln k or ln α vs. 1/. T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpically driven, but entropically driven separation was also observed. The sequence of elution of the enantiomers on the pseudo-enantiomerically behaving CSPs was determined in all cases.

Original languageEnglish
Pages (from-to)130-139
Number of pages10
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume98
DOIs
Publication statusPublished - 2014

Fingerprint

Cinchona Alkaloids
Enantiomers
Carboxylic Acids
Thermal effects
Phase composition
Temperature
Quinidine
Quinine
Sulfonic Acids
Thermodynamics
Acids
Liquids
bicyclo(2.2.2)octane
Experiments

Keywords

  • Bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids
  • Enantiomer separation
  • HPLC
  • Temperature effect
  • Zwitterionic chiral stationary phases

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Spectroscopy
  • Clinical Biochemistry
  • Medicine(all)

Cite this

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abstract = "Procedures for the direct high-performance liquid chromatographic enantiomer separation of four bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids were developed in polar-ionic mode on zwitterionic chiral stationary phases (CSPs) based on cinchonane alkaloide quinine, quinidine and chiral sulfonic acid motifs. The effects of the mobile phase composition including the type of acid and base additives, the structures of the analytes and temperature were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 10-50. °C in order to study the effects of temperature, and thermodynamic parameters were calculated from plots of ln k or ln α vs. 1/. T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpically driven, but entropically driven separation was also observed. The sequence of elution of the enantiomers on the pseudo-enantiomerically behaving CSPs was determined in all cases.",
keywords = "Bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids, Enantiomer separation, HPLC, Temperature effect, Zwitterionic chiral stationary phases",
author = "I. Ilisz and N{\'o}ra Grecs{\'o} and M{\'a}rta Palk{\'o} and F. F{\"u}l{\"o}p and Wolfgang Lindner and A. P{\'e}ter",
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T1 - Structural and temperature effects on enantiomer separations of bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids on cinchona alkaloid-based zwitterionic chiral stationary phases

AU - Ilisz, I.

AU - Grecsó, Nóra

AU - Palkó, Márta

AU - Fülöp, F.

AU - Lindner, Wolfgang

AU - Péter, A.

PY - 2014

Y1 - 2014

N2 - Procedures for the direct high-performance liquid chromatographic enantiomer separation of four bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids were developed in polar-ionic mode on zwitterionic chiral stationary phases (CSPs) based on cinchonane alkaloide quinine, quinidine and chiral sulfonic acid motifs. The effects of the mobile phase composition including the type of acid and base additives, the structures of the analytes and temperature were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 10-50. °C in order to study the effects of temperature, and thermodynamic parameters were calculated from plots of ln k or ln α vs. 1/. T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpically driven, but entropically driven separation was also observed. The sequence of elution of the enantiomers on the pseudo-enantiomerically behaving CSPs was determined in all cases.

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