Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior

I. Ilisz, Zsanett Gecse, Zoltán Pataj, F. Fülöp, Géza Tóth, Wolfgang Lindner, A. Péter

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresolution were investigated. To study the effects of temperature and to obtain thermodynamic parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55. °C. The thermodynamic parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed. The sequence of elution of the enantiomers was determined in most cases.

Original languageEnglish
Pages (from-to)169-177
Number of pages9
JournalJournal of Chromatography A
Volume1363
DOIs
Publication statusPublished - Oct 10 2014

Fingerprint

Cinchona Alkaloids
Imino Acids
Thermodynamics
Temperature
Cyclic Amino Acids
Liquids
Quinidine
Quinine
Ion exchangers
Enantiomers
Entropy
Phase composition
Enthalpy
Ions
Acids
Experiments

Keywords

  • Column liquid chromatography
  • Quinine- and quinidine-based chiral zwitterionic ion-exchanger selectors
  • Unusual secondary amino acids
  • Unusual temperature behavior

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

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title = "Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior",
abstract = "Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresolution were investigated. To study the effects of temperature and to obtain thermodynamic parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55. °C. The thermodynamic parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed. The sequence of elution of the enantiomers was determined in most cases.",
keywords = "Column liquid chromatography, Quinine- and quinidine-based chiral zwitterionic ion-exchanger selectors, Unusual secondary amino acids, Unusual temperature behavior",
author = "I. Ilisz and Zsanett Gecse and Zolt{\'a}n Pataj and F. F{\"u}l{\"o}p and G{\'e}za T{\'o}th and Wolfgang Lindner and A. P{\'e}ter",
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T1 - Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior

AU - Ilisz, I.

AU - Gecse, Zsanett

AU - Pataj, Zoltán

AU - Fülöp, F.

AU - Tóth, Géza

AU - Lindner, Wolfgang

AU - Péter, A.

PY - 2014/10/10

Y1 - 2014/10/10

N2 - Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresolution were investigated. To study the effects of temperature and to obtain thermodynamic parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55. °C. The thermodynamic parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed. The sequence of elution of the enantiomers was determined in most cases.

AB - Two chiral stationary phases containing a quinine- or a quinidine-based zwitterionic ion-exchanger as chiral selector were applied for the enantioseparation of 27 unusual cyclic secondary α-amino acids. The effects of the nature and concentration of the bulk solvent, the acid and base additives, the structures of the analytes and temperature on the enantioresolution were investigated. To study the effects of temperature and to obtain thermodynamic parameters, experiments were carried out at constant mobile phase compositions in the temperature range -5 to 55. °C. The thermodynamic parameters indicated that in most cases the separations were enthalpy-driven, but some entropy-driven separations were also observed. The sequence of elution of the enantiomers was determined in most cases.

KW - Column liquid chromatography

KW - Quinine- and quinidine-based chiral zwitterionic ion-exchanger selectors

KW - Unusual secondary amino acids

KW - Unusual temperature behavior

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