Abstract
AbstractHeparan sulfate (HS) and its structurally related heparin (HP) belong to the family of glycosaminoglycans. HS, distributed on the cell surface as well as the extracellular matrix, plays significant roles in a diverse set of biological processes, including virus infection, cell growth and tumor metastasis. HP is found only in mast cells and some hematopoietic cells and is widely used as an anticoagulant drug. There is a rapid growing interest in the structure and function of heparin sulfate whose heterogeneity enables these molecules to participate in various processes in the body. Although HP and HS have similar structural skeletons, their biological roles in vivo are quite different. To tackle this problem, we have made a lot of efforts to synthesize the whole set of HP/HS disaccharides and trisaccharides. This dissertation focuses on the synthesis of twelve HP/HS disaccharides.The glycosyl acceptor was successfully synthesized in an eight-step procedure which is successfully developed in our laboratory. Coupling of the acceptor with the donor gave the α-linked disaccharide. The common intermediate disaccharide 1 and 2 could be afforded through functional group transformation. With the common intermediate disaccharide 1 and 2 in hand, the final twelve HP/HS disaccharides could be generated by the subsequent deprotection and sulfonation in several steps.