SYNTHESIS OF GLYCOSAMINOGLYCANS

Glycosaminoglycans (GAGs) are a family of complex polyanionic polysaccharides best known for their hexosamine-containing disaccharide repeating units. Based on structural features, GAGs can be classified into four major groups: hyaluronan or hyaluronic acid (HA), chondroitin sulfate (CS) and dermatan sulfate (DS), heparin and heparan sulfate (HS), and keratan sulfate (KS). Structure–activity relationship (SAR) evaluations are needed to understand the extent of binding and the specific nature of the binding sites within the GAG chain. The utmost precision of chemical synthesis in defining the length and functionalization patterns ensures a prominent role in GAG acquisition for SAR studies. GAG syntheses remain formidable, but recent advances are instrumental in providing the necessary compounds with increasing complexity and relative ease. This chapter describes the chemical strategies that are currently utilized for the acquisition of GAG-based oligosaccharides and their mimics.