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Automated glycan assembly of mycobacterial hexaarabinofuranoside and docosasaccharide arabinan (Araf23) motifs found on mycobacterium tuberculosis

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Sabbavarapu,  Narayana Murthy       
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.       
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Sabbavarapu, N. M., & Seeberger, P. H. (2023). Automated glycan assembly of mycobacterial hexaarabinofuranoside and docosasaccharide arabinan (Araf23) motifs found on mycobacterium tuberculosis. Chemistry – A European Journal, 29(23): e202300032. doi:10.1002/chem.202300032.


Cite as: https://hdl.handle.net/21.11116/0000-000C-90A1-A
Abstract
Mycobacteria are covered in a thick layer of different polysaccharides that helps to avert the innate immune response. Lipoarabinomannan (LAM) and arabinogalactan (AG) are ubiquitously contained in these envelopes and rapid access to defined oligo- and polysaccharides is essential to elucidate their structural and biological roles. Arabinofuranose (Araf)residues in LAM and AG are connected either via α-1,2-trans linkages that are synthetically straightforward to install or the more challenging β-(1,2-cis) linkages. Here, we demonstrate that automated glycan assembly (AGA) can be used to quickly prepare 1,2-cis-β-Araf as illustrated by the assembly of a highly branched arabinan hexasaccharide and a docosasaccharide arabinan (Araf23) motif