Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium kansasii

The outer surfaces of mycobacteria, including the organism that causes tuberculosis, are decorated with an array immunomodulatory glycans. Among these lipooligosaccharides (LOSs), a class molecules for which function remains poorly understood. We describe chemical synthesis glycan portion tridecasaccharide LOS from opportunistic pathogen Mycobacterium kansasii. target contains number unusual structural motifs complicate its assembly and is most complex mycobacterial to be synthesized date when considering size unique monosaccharides glycosidic linkages. These studies not only provide roadmap preparation additional members this family glycans, but also provides valuable probe use in structure–activity relationship investigations.