Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium kansasii
- 23 September 2021
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 60 (47), 24859-24863
- https://doi.org/10.1002/anie.202111549
Abstract
The outer surfaces of mycobacteria, including the organism that causes tuberculosis, are decorated with an array of immunomodulatory glycans. Among these are lipooligosaccharides (LOS), a class of molecules for which the function remains poorly understood. We describe the chemical synthesis of the glycan portion of a tridecasaccharide LOS (2) from the opportunistic pathogen Mycobacterium kansasii. The target contains a number of unusual structural motifs that complicate its assembly. This report describes the first syntheses related to M. kansasii LOSs and 2 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 investigationsFunding Information
- Bill and Melinda Gates Foundation (OPP1039665)
- Canadian Institutes of Health Research (201110)
- Natural Sciences and Engineering Research Council of Canada (G121210930)
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