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Enantioseparation of underivatised amino acids by ligand exchange capillary electrophoresis in a counter-electroosmotic mode

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Abstract

Enantiomer separations of underivatised amino acids were carried out by using ligand exchange capillary electrophoresis (LECE). Chiral discrimination is based on the formation of ternary complexes between copper(II), a chiral selector (L-proline or trans-4-hydroxy-L-proline) and an amino acid. All amino acids containing aromatic moieties or not were detected at 214 nm because of their interactions with copper(II). In order to reduce copper(II) adsorption onto capillary walls, we used hexadimethrine bromide to reverse the electroosmotic flow. Using this original strategy, the studied enantiomers migrated in the opposite direction of the anodic electroosmosis. After optimising the analytical conditions taking into account the chiral resolution and the detection sensitivity, we performed very satisfactory enantioseparations not only of aromatic amino acids (tryptophan, tyrosine, phenylalanine and histidine) but also of aliphatic amino acids (threonine, serine, isoleucine and valine). These enantioseparations were performed in a short analysis time at 35 °C. In order to rationalise the obtained results, we evaluated the complexation constants corresponding to the formed ternary complexes by capillary electrophoresis and we used molecular mechanics modelling.

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Acknowledgments

The authors want to thank the Centre de Ressources Informatiques de Haute-Normandie (CRIHAN, Saint-Etienne du Rouvray, France) for software optimisation and technical support.

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Authors and Affiliations

  1. Laboratoire d’Analyse des Systèmes Organiques Complexes, IRCOF and IFRMP, Université de Rouen, 55 rue Saint Germain, 27000, Evreux, France

    Abderrahim Aït Adoubel, Christophe J. Morin, Nadine Mofaddel & Paul-Louis Desbène

  2. UMR 6014 Chimie Organique, Bioorganique: Réactivité et Analyse (COBRA), Université de Rouen, rue Tesnière, 76130, Mont Saint Aignan, France

    Georges Dupas

Authors
  1. Abderrahim Aït Adoubel
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  2. Christophe J. Morin
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  3. Nadine Mofaddel
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  4. Georges Dupas
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  5. Paul-Louis Desbène
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Correspondence to Paul-Louis Desbène.

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Aït Adoubel, A., Morin, C.J., Mofaddel, N. et al. Enantioseparation of underivatised amino acids by ligand exchange capillary electrophoresis in a counter-electroosmotic mode. Anal Bioanal Chem 394, 597–608 (2009). https://doi.org/10.1007/s00216-009-2694-z

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  • DOI: https://doi.org/10.1007/s00216-009-2694-z

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