Electronic Thesis and Dissertation Repository


Master of Science




Dr. Elizabeth Gillies


Carbohydrates are implicated in a large number of biological processes ranging from cell-cell interactions to bacterial and viral infection. Lectins are carbohydrate-binding proteins that are generally specific for certain sugars. However, typical carbohydrate–lectin interactions tend to have very low monomeric binding affinities. In many cases, the binding of saccharide ligands by protein receptors can be improved significantly through the attachment of multiple saccharide residues to a common support. Dendronized polymers constitute a class of macromolecules whose nanoscale size, rigidity, and functionality can be controlled with precision by tuning their molecular architecture. It is hypothesized that due to their large size and tunable properties, carbohydrate-functionalized dendronized polymers can be designed to be highly efficient ligands for lectins. In the current work, we generated a library of dendronized polymers, with different generations of mannose-terminated dendrons conjugated to a polycaprolactone backbone to study their lectin binding abilities. This work also describes the self-assembly of amphiphilic linear-dendron hybrids synthesized from galactose-functionalized dendrons coupled with a linear polypeptide poly-γ-benzyl-L-glutamate (PBLG). Collectively, this work provides the synthesis and applications of mannose and galactose based glycodendrons and their applications in ultra-high multivalent scaffolds and self-assembled structures for carbohydrate-lectin binding studies