Lipid-bound oligosaccharides in insects.

Membrane preparations from immature stages of the fruit fly Ceratitis capitata catalyze the transfer of mannose from GDP-[14C]mannose into lipid-linked oligosaccharides. These compounds behave as polyprenyl derivatives and their formation is stimulated by the addition of an acidic glycolipid fraction isolated from insects. The mannose-labeled oligosaccharides are attached to the poly-isoprenol by a pyrophosphoryl linkage and can be released by mild acid hydrolysis. The trisaccharide lipid has been partially characterized. The results indicate that the compound is polyprenyl-pyrophosphate-N,N'-diacetylchitobiose-mannose. Incubation of dolichyl phosphate [14C]mannose or lower 14C-labeled oligosaccharide lipids with unlabeled GDP-mannose and the insect enzyme leads to the labeling of a higher lipid-bound oligosaccharide. When UDP-N-acetyl[14C]glucosamine was incubated with insect membranes a 14C-labeled chitobiosyl lipid was synthesized. If unlabeled GDP-mannose was also present, the 14C label appeared in the trisaccharide and higher oligosaccharide lipids. Preliminary evidence indicates that the insect polyprenyl oligosaccharides described here might participate in glycoprotein biosynthesis.