Novel aspects of interaction between UDP-Gal and GlcNAc β-1,4-Galactosyltransferase: Transferability and remarkable inhibitory activity of UDP-(mono-O-methylated Gal), UDP-Fuc and UDP-Man Original Research Article

Four mono-O-methylated and one mono-O-acetylated UDP-d-Gal analogues and UDP-l-Fuc were synthesized. 2-O-Methyl-d-galactose residue was enzymatically transferred to give 2′-O-methyllactosaminide in high yield. UDP-Fuc and UDP-Man showed potent inhibitory activities against β-1,4-galactosyltransferase. Structural requirement and steric allowance for the ground and transition states of the enzyme reaction were discussed.