Comparison of alkylglycoside surfactants in enantisseparation by capillary electrophoresis

Yehia Mechref, Ziad El Rassi

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Three alkylglycoside surfactants, namely n-octyl-β-D-glucopyranoside (OG), n-nonyl-β-D-glucopyranoside (NG), and n-octyl-β-D-maltopyranoside (OM), were compared in the enantiomeric separation of dansyl amino acids, binaphthyl phosphate, bupivacaine and warfarin. While only OM exhibited an enantioselectivity toward warfarin, bupivacaine, and dansyl tryptophan, all three surfactants were effective in the enantiomeric resolution of napthyl phosphate and other dansyl amino acids. With the exception of naphthyl phosphate, which could be resolved enantiomerically with OM at surfactant concentrations below the CMC, all solutes required surfactant concentrations greater than the CMC value. This was attributed to the strong hydrophobic association of napthyl phosphate with the OM monomers and to the presence of maltoside residue in the OM surfactant. In general, the optimum surfactant concentration needed for maximum enantiomeric resolution was an inverse function of the hydrophobic character of the solute. Under a given set of conditions, the enantiomeric resolution exhibited by the alkylglycoside surfactants was largely influenced by the extent and loci of solute solubilization into the micelle, and by the nature of the chiral sugar head group of the surfactant.

Original languageEnglish
Pages (from-to)912-918
Number of pages7
JournalELECTROPHORESIS
Volume18
Issue number6
DOIs
StatePublished - Jun 1997

Keywords

  • Alkylglycoside surfactants
  • Binaphthyldiylhydrogen phosphate
  • Bupivacaine
  • Chiral capillary electrophoresis
  • Dansyl amino acids
  • Warfarin

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