SYNTHESIS AND FIBROBLAST GROWTH-FACTOR BINDING OF OLIGOSACCHARIDES RELATED TO HEPARIN AND HEPARAN-SULFATE

A series of six disaccharides, alpha-L-IdoA-(1-->4)-alpha-D-GlcNAc-1-- >OMe alpha-L-IdoA-(1-->4)-alpha-D-GIcNSO(3)-1-->OMe, beta-D-GlcA-(1--> 4)-alpha-D-GlcNAc-1-->OMe, beta-D-GlcA-(1-->4)-alpha-D-GlcNSO(3)-1-->O Me, alpha-D-GlcNAc-(1-->4)-beta-D-GlcA-1-->OMe, beta-D-GlcNAc-(1-->4)- beta-D-GlcA-1--->OMe, and two trisaccharide, 1-->4)-alpha-D-GlcNAc-(1- ->4)-beta-D-GlcA.1-->OMe, ->4)-alpha-D-GlcNSO(3)-(1-->4)-beta-D-GlcA-1 -->Ome was prepared and screened for biological activity in vitro. The oligosaccharides were tested, togetherwith a previously synthesized t risaccharide, 1-->4)-alpha-D-GlcNAc-(1-->4)-beta-D-GlcA-1-->Ome, and t hree tetrasaccharides, NAc-(1-->4)-beta-D-GlcA-(1-->3-beta-D-Gal-1-->O me, >3)-beta-D-Gal-(1-->3)020PO(3)-beta-D-Xyl-1-->Ome, D-Gal-(1-->3)-b eta-Gal-(1-->3)-beta-D-Xyl-1-->Ome, for competitive binding to acidic and basic fibroblast growth factor in an assay using I-125 labelled he parin. It was found that the non-sulphated trisaccharides, (1-->4)-alp ha-D-GlcNAc-(1-->4)-beta-D-GlcA-1-->OMe and 1-->4)-alpha-D-GlcNAc-(1-- >4)-beta-D-GlcA-1-->OMe, and two of the disaccharides can bind to acid ic as well as basic FGF.