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Synthesis of the tetrasaccharide lipid intermediate P1-Dolichyl P2-[O-α-d-mannopyranosyl-(1→6)-O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)- (1→4)-2-acetamido-2-deoxy-α-d-glucopyranosyl] disphosphate

✍ Scribed by Christopher D. Warren; Satoru Nakabayashi; Roger W. Jeanloz

Publisher
Elsevier Science
Year
1987
Tongue
English
Weight
887 KB
Volume
169
Category
Article
ISSN
0008-6215

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✦ Synopsis

O-alpha-D-Mannopyranosyl-(1----6)-O-beta-D-mannopyranosyl-(1----4)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- D-glucopyranose was isolated from bovine or ovine mannosidosis urine. After peracetylation, treatment with trimethylsilyl trifluoromethanesulfonate gave a high yield of a peracetyl oxazoline, which was phosphorylated with dibenzyl phosphate to give a dibenzyl glycosyl phosphate that was converted into a peracetyl tetrasaccharide phosphate by catalytic hydrogenolysis. A coupling reaction with P1-dolichyl P2-diphenyl diphosphate, prepared in two stages from pig-liver dolichol, yielded a peracetyl diphosphoric diester, which on O-deacetylation gave P1-dolichyl P2-[O-alpha-D-mannopyranosyl-(1----6)-O-beta-D-mannopyranosyl-(1----4)-O -(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- alpha-D- glucopyranosyl] diphosphate. This tetrasaccharide lipid intermediate was active as an acceptor of D-mannose residues from GDP-D-mannose in the presence of calf pancreas microsomes.

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