Synthesis of linear-type chondroitin clusters having a C-8 spacer between disaccharide moieties and enzymatic transfer of D-glucuronic acid to the artificial glycans

Newly designed linear-type glycoclusters were synthesized which involve a c hondroitin repeating disaccharide ligand and a hydrophobic octyl ether spac er. The spacer mimics the corresponding disaccharide unit. Repeating elonga tion of the pseudo-tetrasaccharide that was derived from the common cluster unit [--> 8)-octyl-(1 --> 3)-beta -D-Gal-NAc-(1 --> 4)-beta -D-GlcA-(1 --> ] allowed the syntheses of up to the pseudo-decasaccharide analog of chondr oitin. An enzymatic D-GlcA transfer at the non-reducing end of the synthesi zed artificial glycans by GlcATase II was observed. (C) 2001 Published by E lsevier Science Ltd.