title: Synthesis of a Mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy.
abstract: 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.
authors.affiliation: Université Paris-Sud, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR 8182, Laboratoire de Synthèse de Biomolécules, F-91405 Orsay, France.
authors.forename: Aurélie
authors.initials: A
authors.lastname: Lemétais
authors.forename: Yann
authors.initials: Y
authors.lastname: Bourdreux
authors.forename: Philippe
authors.initials: P
authors.lastname: Lesot
authors.forename: Jonathan
authors.initials: J
authors.lastname: Farjon
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Beau
mesh_terms: D016880:Anisotropy; D003903:Deuterium / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000737:chemistry*
chemical_list: D008055:Lipids; C015518:sulfolipids; D003903:Deuterium