Electronic Thesis and Dissertation Repository

Degree

Master of Science

Program

Chemistry

Supervisor

Gillies, Elizabeth R.

Abstract

Carbohydrates are important to cellular communication, recognition, and pathogenesis, making them a useful synthetic target for application in therapeutics and diagnosis. Synthetic carbohydrate presenting scaffolds can replicate or interrupt the binding interactions that occur in nature. Due to the weak nature of the monosaccharide-protein bond, most carbohydrate presenting scaffolds display saccharides in a multivalent manner to improve binding. Recently there has been an effort to combine carbohydrate containing scaffolds with polymersomes (vesicles composed of polymers), due to the structural resemblance of polymersome membranes to biological membranes. This thesis describes the progress towards functionalizing polymersomes with linear glycopolymers as a potential method to achieve improved multivalent binding. A novel beta-D-Galactose containing polymer was synthesized using reversible addition-fragmentation chain transfer polymerization. This polymer, as well as a previously reported glycopolymer based on a polyacrylamide backbone were labeled with rhodamine in order to quantify their subsequent conjugation to the polymersome surface. Two different vesicle platforms were investigated, polybutadiene-b-poly(ethylene glycol) and poly(ethylene glycol)-b-poly(ethyl glyoxylate)-b-poly(ethylene glycol). The experiments suggested that it is possible to conjugate the glycopolymers to the polymersome surfaces to obtain different glycopolymer densities and quantify the reaction yields using fluorescence spectroscopy. Future work will involve binding studies of the glycopolymer-coated vesicles to carbohydrate binding proteins (lectins).

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