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Preparation and enantioseparation characteristics of three chiral stationary phases based on modified β-cyclodextrin for liquid chromatography

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Abstract

In order to study the effect of the nature and the length of the spacer, three mixed 10-undecenoate/phenylcarbamate derivatives of β-cyclodextrin have been prepared and linked to allylsilica gel by means of a radical reaction. The chiral recognition ability of the resulting materials, when used as liquid chromatography chiral stationary phases (CSPs), was evaluated using heptane and either 2-propanol or chloroform as organic mobile-phase modifiers. A large variety of racemic compounds have been separated successfully on these CSPs (mainly pharmaceuticals and herbicides). Optimization of these separations was discussed in terms of mobile-phase composition and structural patterns of the injected analytes. The efficiencies of the three prepared materials were compared to those of previously described perphenylated-β-cyclodextrin column and to analogous cellulose derivative-based CSPs.

Schematic illustration of the b-cyclodextrin/mandelic acid inclusion complex

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Acknowledgements

The authors thank gratefully Pr. Cristina Minguillon (Laboratori de Quimica Farmaceutica, Facultat de Farmacia, Universitat de Barcelona, Avda.Diagonal s/n, E-08028 Barcelona, Spain) and her research group for their valuable collaboration and help.

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Authors and Affiliations

  1. Laboratoire d’Analyse Organique Fonctionnelle, Faculté de Chimie, U.S.T.H.B., B.P. 32, El Alia, Bab Ezzouar, 16111, Alger, Algeria

    Kahina Si-Ahmed, Fairouz Tazerouti & Ahmed Y. Badjah-Hadj-Ahmed

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  1. Kahina Si-Ahmed
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  2. Fairouz Tazerouti
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  3. Ahmed Y. Badjah-Hadj-Ahmed
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Correspondence to Fairouz Tazerouti.

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Si-Ahmed, K., Tazerouti, F. & Badjah-Hadj-Ahmed, A.Y. Preparation and enantioseparation characteristics of three chiral stationary phases based on modified β-cyclodextrin for liquid chromatography. Anal Bioanal Chem 395, 507–518 (2009). https://doi.org/10.1007/s00216-009-2972-9

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