Automated Glycan Assembly of Mycobacterial Hexaarabinofuranoside and Docosasaccharide Arabinan (Araf 23 ) Motifs found on Mycobacterium tuberculosis.

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. Herein, it was demonstrated 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 (Araf 23 ) motif.