Synthesis of linear-type chondroitin clusters having a C8 spacer between disaccharide moieties and enzymatic transfer of d-glucuronic acid to the artificial glycans Original Research Article

Newly designed linear-type glycoclusters were synthesized which involve a chondroitin repeating disaccharide ligand and a hydrophobic octyl ether spacer. The spacer mimics the corresponding disaccharide unit. Repeating elongation of the pseudo-tetrasaccharide that was derived from the common cluster unit [→8)-octyl-(1→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→] allowed the syntheses of up to the pseudo-decasaccharide analog of chondroitin. An enzymatic d-GlcA transfer at the non-reducing end of the synthesized artificial glycans by GlcATase II was observed.