Chromatographia

, Volume 61, Issue 5–6, pp 205–211 | Cite as

Separation of Enantiomers of Isochromene Derivatives by HPLC Using Cyclodextrin-Based Stationary Phases

  • X. Han
  • Q. Zhong
  • D. Yue
  • N. Della Cà
  • R. C. Larock
  • D. W. Armstrong
Article

Abstract

Twenty chiral isochromene derivatives have been chromatographed on native and derivatized cyclodextrin stationary phases using HPLC. The most effective CSPs for the enantioresolution of these analytes in the reverse phase mode are the hydroxypropyl-β-cyclodextrin (Cyclobond RSP), the 2,3-dimethyl-β-cyclodextrin (Cyclobond DM), and the γ-cyclodextrin (Cyclobond II) stationary phases. The α-cyclodextrin (Cyclobond III), β-cyclodextrin (Cyclobond I), acetyl-β-cyclodextrin (Cyclobond AC), S-1-naphthylethyl carbamate-β-cyclodextrin (Cyclobond SN), and 3,5-dimethylphenyl carbamate-β-cyclodextrin (Cyclobond DMP) stationary phases also show enantioselectivities for some analytes. No enantioseparations were observed in the polar organic mode and only a few separations were found in the normal phase mode. The Cyclobond RSP CSP provided the best overall separations of these analytes in the reverse phase mode. The pH of the mobile phase and the nature of organic modifiers have little effect on the enantioresolution. The substituents on the isochromene ring greatly affect the chiral recognition.

Keywords

Column liquid chromatography Cyclodextrin-based phases Enantioseparations Isochromene derivatives 

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Notes

Acknowledgments.

We gratefully acknowledge the support of this work by the National Institutes of Health, NIH RO1 GM53825-08.

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Copyright information

© Friedr. Vieweg&Sohn/GWV Fachverlage GmbH 2005

Authors and Affiliations

  • X. Han
    • 1
  • Q. Zhong
    • 1
  • D. Yue
    • 1
  • N. Della Cà
    • 1
  • R. C. Larock
    • 1
  • D. W. Armstrong
    • 1
  1. 1.Department of ChemistryIowa State UniversityAmesUSA

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