Glycosaminoglycans (GAGs) are perhaps the most complex polymers in nature, and are certainly among the most bioactive, crucial polymers in nature. Their interactions with proteins, in particular, drive a myriad of processes essential to vertebrate life, including blood clotting, development of the central nervous system, cell interactions and motility, and interactions with numerous pathogens. The associated interactions seem, at least in some cases, to be exquisitely specific and dependent on polysaccharide structure. However, due to the extreme complexity of GAG chemical synthesis (typically by lengthy, expensive, ultralow-yield total synthesis building from individual monosaccharides), the mechanisms of these interactions are poorly understood. Even more challenging, though highly attractive, is the concept of being able to manipulate these interactions to address physiological malfunctions. We describe here methodologies for synthesis of complex GAG analogs from simple, inexpensive, readily available polysaccharide derivatives. The efficient methods developed have high regio- and chemoselectivity. These new probes should be valuable for interrogating mechanisms of the important protein-GAG interactions.

Regio- and chemoselective synthesis of glycosaminoglycan analogs from simple precursors

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.