title: Synthesis and anti-mycobacterial activity of glycosyl sulfamides of arabinofuranose.
abstract: A series of arabino N-glycosyl sulfamides, forced to adopt the furanose form by removal of the 5-hydroxyl group, were synthesised as putative isosteric mimics of decaprenolphosphoarabinose, the donor processed by arabinosyltransferases during mycobacterial cell wall assembly. Compounds showed moderate anti-mycobacterial activity, which was maximal for a C10 sulfamide side chain.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz.
authors.forename: Kajitha
authors.initials: K
authors.lastname: Suthagar
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz and Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors.forename: Antony J
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002473:Cell Wall / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D020102:Mycobacterium smegmatis / Q000166:cytology / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D006027:Glycosides; D013449:Sulfonamides; C431714:arabinofuranose; D001089:Arabinose