Synthesis and study of glycoconjugates and carbohydrate based macrocycles

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Carbohydrates are renewable and abundant natural resources. Using readily available sugars such as glucose, fructose, or lactose as building blocks, the research group of Professor Guijun Wang at Old Dominion University is developing new strategies for assembling sugars into large molecules with defined shape and functions. The resulting molecular systems are useful for understanding carbohydrate interactions with other biomolecules. Applications include the discovery of new catalysts and advanced biomaterials. The creation of novel, functional and biocompatible materials from abundant carbohydrates is important for the advancement of green chemistry, material sciences, and biomedical sciences. The project provides educational opportunities for students at all levels, especially undergraduate and graduate students. Students participate in interdisciplinary research in organic synthesis and bioorganic, medicinal, and materials chemistry. Graduate students have industrial internship opportunities in pharmaceutical companies. Low molecular weight gelators (LMWGs) can self-assemble and form reversible supramolecular gels, a category of soft materials with many applications. Professor Wang's group is developing synthetic methods to obtain several classes of glycomimetics that can form reversible hydrogels and organogels and other functional molecular assemblies. The main aims of the proposed research are: 1) The synthesis and study of new series of heterocycle functionalized sugar derivatives that may function as molecular gelators and ligands for catalysis. 2) The functionalization of effective molecular gelators or catalysts to improve their performance through formation of branched or linear oligomers. The multifunctional self-assembling systems are designed to retain the structural flexibility of LMWGs while also displaying mechanical strength and stability. 3) The synthesis and characterization of heterocycle-linked, carbohydrate-based macrocycles. These glycomacrocycles have important potential applications as novel catalysts or enzyme inhibitors.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.