Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors.
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.
Yeoh
Kar Kheng
KK
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Butters
Terry D
TD
Wilkinson
Brendan L
BL
Fairbanks
Antony J
AJ
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*
D014230:Triazoles; D014539:Uridine Diphosphate Sugars; D016695:Glycosyltransferases; D009237:N-Acetyllactosamine Synthase