Synthesis of a Mycobacterium tuberculosis tetra-acylated sulfolipid analogue and characterization of the chiral acyl chains using anisotropic NAD 2D-NMR spectroscopy
| Autor: | Aurélie Lemétais, Yann Bourdreux, Jonathan Farjon, Jean-Marie Beau, Philippe Lesot |
|---|---|
| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
inorganic chemicals
Sulfolipid Magnetic Resonance Spectroscopy Stereochemistry Molecular Conformation 010402 general chemistry 01 natural sciences Catalysis Mycobacterium tuberculosis chemistry.chemical_compound heterocyclic compounds Enantiomeric excess biology 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry organic chemicals Organic Chemistry Nuclear magnetic resonance spectroscopy Deuterium biology.organism_classification Lipids Trehalose 3. Good health 0104 chemical sciences Anisotropy lipids (amino acids peptides and proteins) NAD+ kinase Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2013, 78 (15), pp.7648-57. ⟨10.1021/jo4012255⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo4012255⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|