title: Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates.
abstract: De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in the alkyl chain stopped mutarotation and furanose/pyranose equilibration, allowing the isolation of the first unprotected furanose N-glycosyl sulfonamide.
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.forename: Matthew I J
authors.initials: MI
authors.lastname: Polson
authors.forename: Antony J
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D060326:Chemistry Techniques, Synthetic; D006031:Glycosylation; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D009005:Monosaccharides; D013449:Sulfonamides; D013451:Sulfonic Acids; C005741:sulfamic acid