Synthesis of phosphorylated trimannosides corresponding to end groups of the high-mannose chains of lysosomal enzymes.
Glycosylation of suitably protected 8-methoxycarbonyloctyl alpha-D-manno-pyranosides with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl chloride provided alpha-D-Manp-(1----2)-alpha-D-Man, alpha-D-Manp-(1----3)-alpha-D-Man and alpha-D-Manp-(1----6)-alpha-D-Man derivatives from which the 2'-hydroxyl group was liberated by O-deacetylation. Addition of the terminal D-mannose 6-phosphate residues was achieved by reaction with the readily accessible 2,3,4-tri-O-acetyl-6-O-diphenoxyphosphoryl-alpha-D-mannopyranosyl bromide under standard glycosylation conditions. Conventional deprotection provided the terminal 6"-phosphate of alpha-D-Manp-(1----2)-alpha-D-Manp-(1----2)-alpha-D-Man, alpha-D-Manp-(1----2)-alpha-D-Manp-(1----3)-alpha-D-Man, and alpha-D-Manp-(1----2)-alpha-D-Manp-(1----6)-alpha-D-Man which are present as end groups on the high-mannose oligosaccharide chains of lysosomal enzymes.
D002236:Carbohydrate Conformation; D006867:Hydrolases / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008247:Lysosomes / Q000201:enzymology*; D013403:Sugar Phosphates / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D013403:Sugar Phosphates; D014312:Trisaccharides; D006867:Hydrolases