A spacer-modified disaccharide as a photoaffinity reagent for the acceptor-binding area of bovine (1->4)-β-D-galactosyltransferase: comparison of its acceptor properties with those of other 2-acetamido-2-deoxy-β-D-glucopyranosides

Article abstract of DOI:10.1016/S0008-6215(00)90925-X

The spacer-modified disaccharide 1,10-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-azi-1,10-decanediol (10) that mimics the biantennary core heptasaccharide of N-glycoproteins has been synthesised.Compound 10 is an excellent acceptor in galactosyltransferase-catalysed galactosylation by UDP-galactose, is superior (7-8 fold) to analogues that have only one GlcNAc unit, and is an efficient photoaffinity reagent for galactosyltransferase.In the presence of UDP-Gal, no photoaffinity labelling by 10 takes place, which agrees with the mechanism of galactosyltransferase action.