Synthesis of a homologous series of galactofuranose-containing mycobacterial arabinogalactan fragments

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  • Mycobacteria, including the human pathogen Mycobacterium tuberculosis the causative agent of tuberculosis, produce a complex cell wall structure made of carbohydrates and lipids. The major structural element of the mycobacterial cell wall is a glycoconjugate called the mycolic acid¬–arabinogalactan–peptidoglycan (mAGP) complex. Inhibition of mAGP biosynthesis is a proven strategy for developing anti-mycobacterial drugs and thus understanding the pathways and enzymes involved in the assembly of this molecule is of interest. In this paper we describe the chemical synthesis of a panel nine oligosaccharides fragments (4–12) of the galactan domain of the mAGP complex designed as biosynthetic probes. These structures, ranging in size from a hexasaccharide to a tetradecasaccharide, are potential substrates for two biosynthetic enzymes, GlfT2 and AftA, and represent the largest mycobacterial galactan fragments synthesized to date. The route developed was iterative and provided multi-milligram quantities of the target molecules 4–12 in good overall yield.

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    Attribution-NonCommercial-NoDerivatives 4.0 International