Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

Kar Kheng Yeoh; Terry D Butters; Brendan L Wilkinson; Antony J Fairbanks

doi:10.1016/j.carres.2009.01.001

Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

Carbohydr Res. 2009 Mar 31;344(5):586-91. doi: 10.1016/j.carres.2009.01.001. Epub 2009 Jan 17.

Authors

Kar Kheng Yeoh¹, Terry D Butters, Brendan L Wilkinson, Antony J Fairbanks

Affiliation

¹ Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

PMID: 19233348
DOI: 10.1016/j.carres.2009.01.001

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cattle
Glycosyltransferases / antagonists & inhibitors*
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
N-Acetyllactosamine Synthase / antagonists & inhibitors
Triazoles / chemistry
Uridine Diphosphate Sugars / chemical synthesis*
Uridine Diphosphate Sugars / chemistry
Uridine Diphosphate Sugars / pharmacology*

Substances

Triazoles
Uridine Diphosphate Sugars
Glycosyltransferases
N-Acetyllactosamine Synthase