20210923 Lowary TL Epub

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

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

Angew Chem Int Ed Engl. 2021 Nov 15; 60(47):24859-24863. Epub 2021 Oct 21.
doi: 10.1002/anie.202111549

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Shen K, Bai B, Liu YH, Lowary TL*

摘要

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