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

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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.

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Acknowledgments.

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

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Authors and Affiliations

  1. Department of Chemistry, Iowa State University, Ames, IA, 50011, USA

    X. Han, Q. Zhong, D. Yue, N. Della Cà, R. C. Larock & D. W. Armstrong

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  1. X. Han
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  2. Q. Zhong
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  3. D. Yue
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  4. N. Della Cà
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  5. R. C. Larock
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  6. D. W. Armstrong
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Correspondence to D. W. Armstrong.

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Han, X., Zhong, Q., Yue, D. et al. Separation of Enantiomers of Isochromene Derivatives by HPLC Using Cyclodextrin-Based Stationary Phases. Chroma 61, 205–211 (2005). https://doi.org/10.1365/s10337-004-0478-3

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