Skip to Main content Skip to Navigation
Theses

Phases stationnaires chirales à base de teicoplanine et d'aminoglycosides pour la séparation d'énantiomères d'acides aminés

Abstract : Amino acids are essential chiral elements of life, they have very important biological and pharmacological effects. The separation of amino acids enantiomers is of a crucial importance in various fields such as pharmaceutical industry, agroalimentary, archaeology and forensic sciences. The high performance liquid chromatography (HPLC) using a chiral stationary phase represents at present time the method of choice to separate enantiomers. This work has analyzed the interaction mechanisms involved in the fixation and in the enantioselective separation of tryptophan enantiomers on teicoplanin and teicoplanin aglycone (TAG) chiral stationary phases (CSPs). A comparative thermodynamic study between these two CSPs was performed to investigate the negative role played by the three saccharidic units of the teicoplanin in the chiral discrimination process. Thus, we showed that tryptophan interacts considerably with the aglycone pocket of the teicoplanin. A simple coating method of reversed-phase supports to prepare a new teicoplanin CSP has allowed to separate some aromatic amino acids and to reverse their enantiomeric elution order (L>D) compared to that classically obtained with a teicoplanin covalently immobilized on silica support (D>L). In addition, we have developed a new class of chiral selectors based on aminoglycosides for chiral ligand-exchange chromatography. Several enantiomers of amino acids and nucleosides were separate successfully on this new kind of CSPs.
Document type :
Theses
Complete list of metadatas

Cited literature [43 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-00156850
Contributor : Mohamed Haroun <>
Submitted on : Friday, June 22, 2007 - 10:21:44 PM
Last modification on : Friday, November 6, 2020 - 4:10:16 AM

Identifiers

  • HAL Id : tel-00156850, version 1

Collections

Citation

Mohamed Haroun. Phases stationnaires chirales à base de teicoplanine et d'aminoglycosides pour la séparation d'énantiomères d'acides aminés. Autre. Université Joseph-Fourier - Grenoble I, 2007. Français. ⟨tel-00156850⟩

Share

Metrics

Record views

900

Files downloads

6663