Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues.
The synthesis of a panel of oligosaccharides containing C-5 arabinofuranosyl residues (9-20) is described. These compounds are of interest as potential inhibitors of the alpha-(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 (24-26) and their subsequent coupling to the appropriate acceptor species (21-23). 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.
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA.
Oana M
OM
Cociorva
Todd L
TL
Lowary
D001087:Arabinonucleosides / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000201:enzymology*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010430:Pentosyltransferases / Q000037:antagonists & inhibitors*; D013865:Thioglycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D001087:Arabinonucleosides; D004187:Disaccharides; D009844:Oligosaccharides; D013865:Thioglycosides; D014312:Trisaccharides; D010430:Pentosyltransferases; C101967:arabinosyltransferase