Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium kansasii. (21st October 2021)

• Record Type: Journal Article
• Authors: Shen, Ke; Bai, Bing; Liu, Yu‐Hsuan; Lowary, Todd L.
• Is Part Of: Angewandte Chemie. Volume 133:Number 47(2021)
• Page Start: 25063
• Page End: 25067
• Publication Date: 2021-10-21
• Subjects: antigens -- complex glycans -- lipooligosaccharides -- mycobacteria -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202111549
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : The tridecasaccharide glycan domain of lipooligosaccharides from the opportunistic pathogen Mycobacterium kansasii was synthesized. The target (see structure) possesses structural motifs that make its synthesis a formidable challenge, including rare monosaccharides, an asymmetrically substituted trehalose residue and a base‐sensitive amide side chain. The study provides a strategy for synthesizing other members of this unusual class of molecules.