Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues Original Research Article

The synthesis of a panel of oligosaccharides containing C-5 arabinofuranosyl residues () is described. These compounds are of interest as potential inhibitors of the α-(1 → 5)-arabinosyltransferase involved in the assembly of mycobacterial cell-wall arabinan. In the series of compounds prepared, the 5-OH group on the nonreducing residue(s) is replaced, independently, with an amino, azido, fluoro, or methoxy functionality. The synthesis of the target compounds involved the preparation of a series of C-5 modified arabinofuranosyl thioglycosides () and their subsequent coupling to the appropriate acceptor species (). Deprotection of the glycosylation products afforded the azido, fluoro, or methoxy analogs directly. The amino derivatives were obtained in one additional step by reduction of the azido compounds.