High-performance liquid chromatographic enantioseparation of cationic 1,2,3,4-tetrahydroisoquinoline analogs on Cinchona alkaloid-based zwitterionic chiral stationary phases ABCs 13th Anniversary

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The stereoisomers of 1,2,3,4-tetrahydroisoquinoline analogs were resolved for the first time by applying a polar ionic mobile phase on a quinine or a quinidine moiety fused with a chiral sulfonic acid-type chiral selector immobilized on silica [Chiralpak ZWIX(+)™ and Chiralpak ZWIX(-)™]. The effects of the nature and concentrations of the mobile phase components and additives and temperature on the retention and enantioseparation on the investigated chiral columns were studied. Experiments were performed in the temperature range 10-50 C. Thermodynamic parameters were calculated from plots of ln α versus 1/T. The separations were generally enthalpy-controlled, but entropy-controlled separation was also observed below 30 C. The enantiomer elution order was determined in some cases and was observed to be opposite on the ZWIX(+)™ and ZWIX(-)™ columns. Our results contribute to a better understanding of the enantiorecognition mechanism of chiral bases with chiral zwitterionic selectors.

Original languageEnglish
Pages (from-to)961-972
Number of pages12
JournalAnalytical and Bioanalytical Chemistry
Volume407
Issue number3
DOIs
Publication statusPublished - Jan 24 2015

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Cinchona Alkaloids
Anniversaries and Special Events
Stereoisomerism
Temperature
Quinidine
Quinine
Sulfonic Acids
Enantiomers
Liquids
Entropy
Thermodynamics
Silicon Dioxide
Enthalpy
Experiments
1,2,3,4-tetrahydroisoquinoline

Keywords

  • Enantioseparation of 1,2,3,4-tetrahydroisoquinoline analogs
  • High-performance liquid chromatography
  • Thermodynamics of enantioseparation
  • Zwitterionic selectors

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

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title = "High-performance liquid chromatographic enantioseparation of cationic 1,2,3,4-tetrahydroisoquinoline analogs on Cinchona alkaloid-based zwitterionic chiral stationary phases ABCs 13th Anniversary",
abstract = "The stereoisomers of 1,2,3,4-tetrahydroisoquinoline analogs were resolved for the first time by applying a polar ionic mobile phase on a quinine or a quinidine moiety fused with a chiral sulfonic acid-type chiral selector immobilized on silica [Chiralpak ZWIX(+)™ and Chiralpak ZWIX(-)™]. The effects of the nature and concentrations of the mobile phase components and additives and temperature on the retention and enantioseparation on the investigated chiral columns were studied. Experiments were performed in the temperature range 10-50 C. Thermodynamic parameters were calculated from plots of ln α versus 1/T. The separations were generally enthalpy-controlled, but entropy-controlled separation was also observed below 30 C. The enantiomer elution order was determined in some cases and was observed to be opposite on the ZWIX(+)™ and ZWIX(-)™ columns. Our results contribute to a better understanding of the enantiorecognition mechanism of chiral bases with chiral zwitterionic selectors.",
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AU - Ilisz, I.

AU - Grecsó, Nóra

AU - Fülöp, F.

AU - Lindner, Wolfgang

AU - Péter, A.

PY - 2015/1/24

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N2 - The stereoisomers of 1,2,3,4-tetrahydroisoquinoline analogs were resolved for the first time by applying a polar ionic mobile phase on a quinine or a quinidine moiety fused with a chiral sulfonic acid-type chiral selector immobilized on silica [Chiralpak ZWIX(+)™ and Chiralpak ZWIX(-)™]. The effects of the nature and concentrations of the mobile phase components and additives and temperature on the retention and enantioseparation on the investigated chiral columns were studied. Experiments were performed in the temperature range 10-50 C. Thermodynamic parameters were calculated from plots of ln α versus 1/T. The separations were generally enthalpy-controlled, but entropy-controlled separation was also observed below 30 C. The enantiomer elution order was determined in some cases and was observed to be opposite on the ZWIX(+)™ and ZWIX(-)™ columns. Our results contribute to a better understanding of the enantiorecognition mechanism of chiral bases with chiral zwitterionic selectors.

AB - The stereoisomers of 1,2,3,4-tetrahydroisoquinoline analogs were resolved for the first time by applying a polar ionic mobile phase on a quinine or a quinidine moiety fused with a chiral sulfonic acid-type chiral selector immobilized on silica [Chiralpak ZWIX(+)™ and Chiralpak ZWIX(-)™]. The effects of the nature and concentrations of the mobile phase components and additives and temperature on the retention and enantioseparation on the investigated chiral columns were studied. Experiments were performed in the temperature range 10-50 C. Thermodynamic parameters were calculated from plots of ln α versus 1/T. The separations were generally enthalpy-controlled, but entropy-controlled separation was also observed below 30 C. The enantiomer elution order was determined in some cases and was observed to be opposite on the ZWIX(+)™ and ZWIX(-)™ columns. Our results contribute to a better understanding of the enantiorecognition mechanism of chiral bases with chiral zwitterionic selectors.

KW - Enantioseparation of 1,2,3,4-tetrahydroisoquinoline analogs

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