Reversal of the enantiomeric elution order of some aromatic amino acids using reversed-phase chromatographic supports coated with the teicoplanin chiral selector |
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Authors: | Haroun Mohamed Ravelet Corinne Grosset Catherine Ravel Anne Villet Annick Peyrin Eric |
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Affiliation: | Département de Pharmacochimie Moléculaire UMR 5063 CNRS, Institut de Chimie Moléculaire de Grenoble FR 2607, Université Joseph Fourier, UFR de Pharmacie de Grenoble, Domaine de la Merci, 38700 La Tronche, France |
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Abstract: | In this paper, two chiral stationary phases were prepared by coating the surface of both C8 and C18 high-performance liquid chromatography (HPLC) supports with the teicoplanin chiral selector. The hydrophobic C11 acyl side chain, attached to the d-glucosamine group of teicoplanin, served as anchor moiety for the immobilization of the chiral selector on the apolar support material. The retention and enantioselectivity of these coated stationary phases were studied using some aromatic amino acids as probe solutes and an aqueous solution as mobile phase. It was found that the enantiomer elution order on the modified C8 and C18 stationary phases was reversed (l > d) relatively to that classically observed with a teicoplanin covalently immobilized on a silica support (d > l). Such a dynamic coating on the reversed-phase supports was found to be of interest since the apparent enantioselectivity was not significantly changed by the use during an extended period of time or following a long-term storage of the columns. |
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Keywords: | Chiral separation Teicoplanin Coating Aromatic amino acids |
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