Methyl 3-amino-3-deoxy-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2- deoxy-beta-D-glucopyranoside: an inhibitor of UDP-D-galactose: beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-glucose (1-->3)-alpha-D-galactopyranosyltransferase.
UDP-D-galactose:beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D- glucose alpha-(1-->3)-D-galactopyranosyltransferase [E.C. 2.4.1.151] transfers D-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with Ki = 104 microM. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.
Department of Chemistry, University of Alberta, Edmonton, Canada.
A C
AC
Helland
O
O
Hindsgaul
M M
MM
Palcic
C L
CL
Stults
B A
BA
Macher
D000606:Amino Sugars / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000494:pharmacology; D005700:Galactosyltransferases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008969:Molecular Sequence Data; D014531:Uridine Diphosphate Galactose / Q000737:chemistry*
D000606:Amino Sugars; D004187:Disaccharides; D014531:Uridine Diphosphate Galactose; D005700:Galactosyltransferases