title: Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors.
abstract: A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding alpha-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5mM in an assay against bovine milk beta-1,4-galactosyltransferase.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: Kar Kheng
authors.initials: KK
authors.lastname: Yeoh
authors.forename: Terry D
authors.initials: TD
authors.lastname: Butters
authors.forename: Brendan L
authors.initials: BL
authors.lastname: Wilkinson
authors.forename: Antony J
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D000818:Animals; D002417:Cattle; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009237:N-Acetyllactosamine Synthase / Q000037:antagonists & inhibitors; D014230:Triazoles / Q000737:chemistry; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D014230:Triazoles; D014539:Uridine Diphosphate Sugars; D016695:Glycosyltransferases; D009237:N-Acetyllactosamine Synthase