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A persubstituted cationic beta-cyclodextrin for chiral separations

F O'Keeffe1, S A Shamsi, R Darcy

  • 1Department of Chemistry, University College Dublin, Ireland.

Analytical Chemistry
|December 24, 1997
PubMed
Summary
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A novel polycationic beta-cyclodextrin derivative (beta-CD-EA) effectively separates chiral anionic analytes using capillary electrophoresis. Its selectivity is pH-dependent, enabling efficient enantioseparation of drugs and herbicides.

Area of Science:

  • Analytical Chemistry
  • Separation Science
  • Supramolecular Chemistry

Background:

  • Chiral separation is crucial for pharmaceuticals and agrochemicals.
  • Cyclodextrins are widely used chiral selectors.
  • Developing novel cyclodextrin derivatives enhances enantioseparation capabilities.

Purpose of the Study:

  • To present the application of a novel polycationic beta-cyclodextrin derivative, heptakis(6-hydroxyethylamino-6-deoxy-beta-cyclodextrin) (beta-CD-EA).
  • To evaluate beta-CD-EA as a chiral host-guest additive for enantioseparation of anionic analytes.
  • To investigate the influence of pH on chiral selectivity and electrophoretic mobility.

Main Methods:

  • Capillary Zone Electrophoresis (CZE) with a novel polycationic beta-cyclodextrin (beta-CD-EA) additive.

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  • Utilizing a reverse polarity configuration.
  • Adjusting the pH of the background electrolyte to optimize chiral selectivity.

    • Main Results:

    • beta-CD-EA demonstrated effective enantioseparation for various chiral anionic analytes, including drugs and herbicides.
    • Enantioseparation of anti-inflammatory agents (fenoprofen, flurbiprofen, ibuprofen) achieved at pH 5.0.
    • Efficient separation of six structurally related anionic herbicides in approximately 15 minutes at pH 6.0 or 7.0.

    Conclusions:

    • The pH-tunable electrophoretic mobility of beta-CD-EA allows for adjustable chiral selectivity.
    • beta-CD-EA is a versatile and effective chiral selector for capillary electrophoresis.
    • This novel cationic cyclodextrin derivative shows significant potential for analytical chiral separations.