Tuberculosis (TB) has been one the most infectious and deadly diseases for decades and is nowadays responsible for the death of 1.7 M people annually. The thick hydrophobic cell wall of the microorganism responsible for TB, Mycobacterium tuberculosis (M.tb), is the main reason for its persistence, creating an impermeable barrier for antibiotics.An interesting compound found only in the cell wall of M.tb is di-acylsulfoglycolipid (Ac2SGL). Ac2SGL was recognized to function as a mycobacterial antigen able to activate T-cells which in turn can release interferon-?, kill mycobacteria in vitro and recognize infected antigen presenting cells.For these reasons, Ac2SGL could be of interest for a TB vaccine.In light of all these appealing properties we aimed for the first asymmetric synthesis of Ac2SGL. A prerequisite was to elucidate the absolute stereochemistry of the hydroxyl group at C-17 vicinal to the 1,3-polymethyl array. In the presentation we will present how we unraveled the stereochemistry using NMR and HPLC studies. Additionally, two approaches towards the synthesis of the 1,3-methyl substituted fatty acid (hydroxyphthioceranic acid) and its regioselective introduction to the trehalose core will be discussed.

Synthesis and structure elucidation of Ac<sub>2</sub>SGL: A sulfoglycolipid from <i>Mycobacterium tuberculosis</i>

243rd National Meeting (2012)

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Synthesis and structure elucidation of Ac2SGL: A sulfoglycolipid from Mycobacterium tuberculosis

Synthesis and structure elucidation of Ac₂SGL: A sulfoglycolipid from Mycobacterium tuberculosis