title: Direct aqueous synthesis of non-protected glycosyl sulfoxides; weak inhibitory activity against glycosidases.
abstract: A flavinium catalyst, in conjunction with hydrogen peroxide as stoichiometric oxidant, allowed the aqueous conversion of non-protected thioglycosides into the corresponding glycosyl sulfoxides. These glycosyl sulfoxides displayed only very weak inhibitory activity against corresponding glycosidases.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors.forename: Stewart R
authors.initials: SR
authors.lastname: Alexander
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors.forename: Andrew J A
authors.initials: AJ
authors.lastname: Watson
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand; Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. Electronic address: antony.fairbanks@canterbury.ac.nz.
authors.forename: Antony J
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D060326:Chemistry Techniques, Synthetic; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006031:Glycosylation; D006861:Hydrogen Peroxide / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013865:Thioglycosides / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D016877:Oxidants; D013454:Sulfoxides; D013865:Thioglycosides; D014867:Water; D006861:Hydrogen Peroxide; D006026:Glycoside Hydrolases
keywords: Biomimetic catalysis; Glycosidase inhibition; Glycosyl sulfoxide; Oxidation; Thioglycoside