Cyclodextrin-mediated enantioseparation of phenylalanine amide derivatives and amino alcohols by capillary electrophoresis-Role of complexation constants and complex mobilities

Anita Aranyi, Antal Péter, István Ilisz, Ferenc Fülöp, Gerhard K.E. Scriba

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The separation of the enantiomers of phenylalanine amide and N-methyl derivatives as well as some amino alcohols was studied by CE in acidic BGEs using CDs as chiral selectors. The native CDs displayed only low chiral recognition ability at a concentration of 15 mg/mL in 20 mM sodium phosphate buffer, pH 2.5. In contrast, the analyte enantiomers were separated in the presence of randomly sulfated CDs under reversed polarity of the applied voltage. Sulfated β-CD proved to be the most universal selector resulting in the enantioseparation of all analytes. Opposite enantiomer migration order depending on the size of the CD cavity was observed for phenylalanine amide and 2-amino-2-phenylethanol. The R-enantiomers migrated first in the presence of sulfated α-CD and γ-CD while the S-enantiomers were detected first in the presence of sulfated β-CD. The enantioseparations could be rationalized based on analyte complexation by the respective CDs except for 2-amino-2-phenylethanol and sulfated β-CD where essentially equal complexation constants were derived for the enantiomers. In this case, the migration behavior could be attributed to the mobilities of the enantiomer-CD complexes adding another example to the CE-specific phenomenon of enantioseparations based primarily on complexmobilities.

Original languageEnglish
Pages (from-to)2848-2854
Number of pages7
JournalELECTROPHORESIS
Volume35
Issue number19
DOIs
Publication statusPublished - Jan 1 2014

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Keywords

  • Amino alcohol
  • Binding constants
  • Enantiomer separation
  • Highly sulfated cyclodextrin
  • Phenylalanine amide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

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