Streptavidin chiral stationary phase for the separation of adenosine enantiomers |
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Authors: | Ravelet Corinne Michaud Michael Ravel Anne Grosset Catherine Villet Annick Peyrin Eric |
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Institution: | Département de Pharmacochimie Moléculaire UMR 5063 CNRS-UJF, Equipe de Chimie Analytique, Université Joseph Fourier, ICMG FR 2607, UFR de Pharmacie de Grenoble, Avenue de Verdun, 38240 Meylan, France. |
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Abstract: | In this paper, a microbore column packed with streptavidin particles was used, at various temperatures (0-24 degrees C), to separate the adenosine enantiomers by HPLC. Using an aqueous mobile phase, the apparent enantioseparation was high for a small molecule, varying from 11.5 at 0 degrees C to 6.2 at 24 degrees C. From the experiments carried out with a streptavidin-biotin complex stationary phase, it was demonstrated that the blockage of the biotin sites of the immobilized streptavidin was responsible for a strong decrease in the enantioselectivity via a direct and/or an indirect effect. From the analysis of the concentration dependencies of the solute retention factor, it was also shown that a reduction of the D-adenosine specific binding sites occurred at the lowest temperature. The thermodynamic parameters determined from the van't Hoff plots indicated that the D-adenosine binding to the streptavidin specific sites was enthalpically driven. |
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Keywords: | Enantiomer separation Chiral stationary phase LC Adenosine Streptavidin |
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