BUILDING UNITS OF OLIGOSACCHARIDES .110. SYNTHESIS OF POTENTIAL INHIBITORS OF N-ACETYLGLUCOSAMINYLTRANSFERASE-I

Modified derivatives of the trisaccharide octyl alpha-D-Man-(1--> 3)-[ alpha-D-Man(1-->6)]-beta-D-Man were synthesized by attaching reactive groups via a pentyl spacer to the 4'-OH and 6'-OH group. Glycosylation steps were carried out by using the trichloroacetimidate method with suitable building blocks. The compounds substituted at 6'-OH are of sp ecial interest. The epoxide 27 and the diazirine 25 are reversible inh ibitors of N-acetylglucosaminyltransferase I (GlcNAc-T I). Product 26 with a spacer-linked iodoacetamide is an irreversible inhibitor of Glc NAc-T I.