High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase

Róbert Berkecz, Anita Sztojkov-Ivanov, István Ilisz, Eniko Forró, Ferenc Fülöp, Myung Ho Hyun, Antal Péter

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Abstract

Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of 14 unnatural β-amino acids, including several β-3-homo-amino acids on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid bonded to 3-aminopropyl silica gel as chiral selector. The effects of the organic and the acidic modifiers and the mobile phase composition on the separation were investigated. The natures and positions of the substituents on the aromatic ring substantially influenced the retention and enantioseparation. The elution sequence in most cases was determined and the R enantiomers were eluteted before the S enantiomers.

Original languageEnglish
Pages (from-to)138-143
Number of pages6
JournalJournal of Chromatography A
Volume1125
Issue number1
DOIs
Publication statusPublished - Aug 25 2006

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Keywords

  • (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase
  • Column liquid chromatography
  • β-Amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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