The synthesis of glycodendrimers and their applications in carbohydrate-protein interactions and catalysis
Morgan, Joel Ryan.
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Glycodendrimers were synthesized for studies in carbohydrate-protein interactions, and from these studies we gained insight into the mechanism of some carbohydrate-protein interactions. First, the synthesis of tris-mannose cluster functionalized glycodendrimers of different sizes using a 'click chemistry' approach is described. The macromolecules were characterized using 1H and 13C NMR and MALDITOF MS. Next, a heterogeneous dendrimer functionalization strategy to control the presentation of the carbohydrate clusters around the dendrimer periphery is reported. Nacetyl galactosamine and phenyl azide heterogeneously functionalized PAMAM dendrimers were synthesized and used as macromonomers in a 'click chemistry' polymerization reaction. The dendritic polymer was designed as a lipid raft microdomain mimic.Next, the synthesis dimannose functionalized PAMAM dendrimers for evaluation of binding with Cyanovirin N, an HIV inactivating protein is described. These glycodendrimers and others were evaluated in protein binding experiments using transmission electron microscopy, precipitation assays, isothermal titration microcalorimetry, and a hemagglutination inhibition assay. This work represents advancements in the synthesis of glycodendrimers with new carbohydrate architectures. Also, the results of the protein binding studies afforded insight into the mechanism of carbohydrate-protein interactions. Poly(polyoxometalate) metallodendrimers were synthesized and characterized using 31P NMR, transmission electron microscopy and MALDI-TOF MS. Polyoxometalates and poly(polyoxometalate) dendrimers were analyzed as oxidation catalysts.