Chondroitin sulfates (CSs) are polyanionic complex polysaccharides consist of a disaccharide repeating unit of D-glucuronic acid (GlcA) β-1,3- linked to 2-acetamido-2-deoxy-D-galactosamine (GalN). CSs belong to glycosaminoglycans (GAGs) family and exist as a part of chondroitin sulfate proteoglycans (CSPGs). In CSPG, CSs are covalently conjugated to the hydroxyl group of serine amino acid in the core protein trough a tetrasaccharide linker of GlcA-β-1,3-galacose (Gal)-β-1,3-Gal-β-1,4-xylose. CS and CSPG interact with a large variety of biological molecules such as growth factors, chemokines, Aβ, and cell adhesion molecules. To date, no methods are available to allow the access of CSPG bearing homogenous glycan chains. In this presentation, we will discuss the chemical synthesis of Syndecan-1 chondroitin sulfate glycopeptide which was synthesized for the first time using the cassette approach. The sequence of glycosylation to form the octasaccharide serine cassette was critical. The glycopeptide was successfully assembled via a 2+(3+3) glycosylation strategy followed by peptide chain elongation.

Effort toward assembly of chondroitin sulfate A bearing syndecan-1 glycopeptide

256th National Meeting (2018)

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