Transfer of D-galactosyl groups to 6-O-substituted 2-acetamido-2-deoxy-D-glucose residues by use of bovine D-galactosyltransferase.
Bovine D-galactosyltransferase was found to transfer D-galactose from UDP-galactose to 6-O-substituted 2-acetamido-2-deoxy-beta-D-glucopyranosides. The resulting 6-O-substituted N-acetyllactosamines were readily synthesized in milligram amounts and conveniently isolated on a reverse-phase support when prepared as the 8-methoxycarbonyloctyl glycosides. The 6-O-substitution tolerated by the enzyme include an alpha-L-fucopyranosyl group and the methyl ester of alpha-linked N-acetylneuraminic acid, but not the free acid itself. The product trisaccharides were characterized by 1H-n.m.r. spectroscopy and fast-atom-bombardment mass spectrometry.
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D000818:Animals; D002417:Cattle; D005260:Female; D005700:Galactosyltransferases / Q000378:metabolism*; D005944:Glucosamine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D007700:Kinetics; D008892:Milk / Q000201:enzymology; D013379:Substrate Specificity; D014531:Uridine Diphosphate Galactose / Q000378:metabolism*; D014539:Uridine Diphosphate Sugars / Q000378:metabolism*
D007202:Indicators and Reagents; D014539:Uridine Diphosphate Sugars; D014531:Uridine Diphosphate Galactose; D005700:Galactosyltransferases; D005944:Glucosamine; D000117:Acetylglucosamine