SYNTHESIS OF 8-METHOXYCARBONYLOCTYL BETA-GLYCOSIDES OF TRISACCHARIDESAND TETRASACCHARIDES RELATED TO SCHIZOPHYLLAN AND NEOGLYCOPROTEINS THEREFROM

The 8-methoxycarbonyloctyl beta-glycosides of the trisaccharides O-bet a-D-Glcp-(1-->6) O-beta-D-Glcp-(1-->3)-D-Glcp and beta-D-Glcp-(1-->3)- O-[beta-D-Glcp-(1-->6)]-D-Glcp and of the tetrasaccharide cp-(1-->3)-O -[beta-D-Glcp-(1-->6)]-O-beta-D-Glcp-( 1-->3)-D-Glcp, corresponding to the fragments of schizophyllan, have been synthesized by using mono- to tetrasaccharide 1-thioglycosides as glycosyl donors, each bearing a participating benzoyl group in the 2-position, and N-iodosuccinimide and silver triflate as promoter. Saponification of the tri- and tetras accharide beta-glycosides, followed by attachment to bovine serum albu min of the resulting sugar derivatives having a carboxyl group at the aglycon terminal, provided neoglycoproteins for immunological studies of the polysaccharide.