Synthesis of a Mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2013

Synthesis of a Mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy.

Aurélie Lemétais
  • Fonction : Auteur
Yann Bourdreux
Philippe Lesot
Jonathan Farjon

Résumé

Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated trehalose sulfate derivatives having simple acyl chains. The trehalose core was regioselectively protected using a tandem procedure with catalytic iron(III) chloride hexahydrate and further desymmetrized. Model chiral fatty acids, prepared by a zinc-mediated cross-coupling, were incorporated into the trehalose core. The enantiomeric excess of the chiral fatty acids has been measured by natural abundance deuterium (NAD) 2D-NMR spectroscopy in a polypeptide based chiral liquid crystal. The synthetic approach established for the model compounds can easily be developed for the preparation of other analogues and natural sulfolipids.

Domaines

Chimie organique
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Dates et versions

hal-00910978 , version 1 (28-11-2013)

Identifiants

Citer

Aurélie Lemétais, Yann Bourdreux, Philippe Lesot, Jonathan Farjon, Jean-Marie Beau. Synthesis of a Mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy.. Journal of Organic Chemistry, 2013, 78 (15), pp.7648-57. ⟨10.1021/jo4012255⟩. ⟨hal-00910978⟩
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