Synthesis of Oligosaccharides Structurally Related to Hyaluronic Acid Fragments

摘要

Hyaluronic acid (HA) is a natural polysaccharide constructed from the alternating residues of beta-D-glucuronic acid and N-acetyl-beta-D-glucosamine. Being a component of glycoproteins and proteoglycans, HA performs important functions in living organisms. For example, HA plays a key role in the development of cell division and migration, vascular formation, inflammation, and oncogenesis. The review summarizes the successfully accomplished syntheses of oligosaccharides related to HA chains, an analysis of strategies for assembling the corresponding carbohydrate chains, and the evaluation of types of the used glycosyl-donors and glycosyl-acceptors, as well as strategies for choosing protective groups in the synthetic blocks. The use of enzymatic splitting of natural samples of HA and chondroitin sulfate in the work to produce appropriate low-molecular-weight oligosaccharides is also considered. Synthesized oligosaccharides and glycoconjugates based on them are valuable models for establishing a relationship between the structure and biological properties of HA and for developing approaches to the production of therapeutic drugs based on HA, including those for wound healing and treatment of inflammatory processes, as well as inhibitors of certain stages of oncogenesis.