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: Aurélie Lemétais, Yann Bourdreux, Philippe Lesot, Jonathan Farjon, Jean-Marie Beau
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 78 Issue 15 Pg. 7648-57 (Aug 02 2013) ISSN: 1520-6904 [Electronic] United States
• PMID: 23845048 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Lipids
• sulfolipids
• Deuterium

Topics

• Anisotropy
• Deuterium (chemistry)
• Lipids (chemical synthesis, chemistry)
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Mycobacterium tuberculosis (chemistry)