High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on (+)-(18-crown-6)-2,3, 11,12-tetracarboxylic acid-based chiral stationary phases

László Sipos, I. Ilisz, Anita Aranyi, Zsanett Gecse, Melinda Nonn, F. Fülöp, Myung Ho Hyun, A. Péter

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The enantiomers of four unusual isoxazoline-fused 2- aminocyclopentanecarboxylic acids were directly separated on chiral stationary phases containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The nature of the alcoholic modifier (MeOH, EtOH, IPA) exerted a great effect on the retention, whereas the selectivity and resolution did not change substantially. Two types of dependence of retention on alcohol content were detected: k1 increased continuously with increasing alcohol content or a U-shaped retention curve was observed. A comparison of the chromatographic data obtained with HCOOH, AcOH, TFA, HClO4, H2SO 4, or H3PO4 as acidic modifier at a constant concentration demonstrated that in most cases, larger k values were obtained on the application of AcOH or HCOOH, and an increase of the acid content resulted in a decrease of retention. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes and selector. The sequence of elution of the enantiomers was determined in all cases.

Original languageEnglish
Pages (from-to)817-824
Number of pages8
JournalChirality
Volume24
Issue number10
DOIs
Publication statusPublished - Oct 2012

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Cycloleucine
Enantiomers
Alcohols
Acids
Liquids
18-crown-6 2,3,11,12-tetracarboxylic acid

Keywords

  • (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phases
  • column liquid chromatography
  • enantiomer separation
  • isoxazoline-fused 2-aminocyclopentanecarboxylic acids

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on (+)-(18-crown-6)-2,3, 11,12-tetracarboxylic acid-based chiral stationary phases. / Sipos, László; Ilisz, I.; Aranyi, Anita; Gecse, Zsanett; Nonn, Melinda; Fülöp, F.; Hyun, Myung Ho; Péter, A.

In: Chirality, Vol. 24, No. 10, 10.2012, p. 817-824.

Research output: Contribution to journalArticle

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