Synthesis and biotinylation of oligosaccharide fragments of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated lipoarabinomannan from Mycobacterium tuberculosis

• An efficient synthesis of 5-deoxy-5-methylthio-xylofuranose (MTX) oligosaccharides is reported.
• Conjugation of synthesized oligosaccharides with biotin to aid biological evaluation was carried out.
• Thioglycoside derivatives have been used as glycosyl donors in the glycosylation reactions.
• Activation of thioglycoside using NIS and AgOTf.

The attachment of biotin to a molecule provides a powerful tool in biology. Here, we report an efficient synthesis and biotinylation of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated Lipoarabinomannan from Mycobacterium tuberculosis. Preparation of the oligosaccharides involved the sequential addition of thioglycoside donors with arabinofuranosyl-containing acceptors. Methylthio group was introduced near the end of the synthesis.

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