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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