Synthesis of star-shaped glycopolymers and their interactions with concanavalin A

Abstract

The focus of this thesis is on the synthesis of glycopolymers via RAFT polymerisation and post-functionalisation techniques. Synthetic routes include direct polymerisation from a glycomonomer, 2-acryloylethyl-2’, 3’, 4’, 6’- tetra-O-acetyl-α-D-mannopyranoside, and post-functionalisation of preformed polymeric scaffolds using functionalised sugar molecules including 1-thio-β-D-glucose sodium salt and 2-bromoethyl-2′,3′,4′,6′, tetra-O-acetyl-α-D-mannopyranoside. In the direct synthesis route, relatively low temperature was used to ensure the integrity of carbohydrate groups; while in the post-functionalisation route thiol-halogen click reactions were used to eliminate hazardous side products. Well-defined glycopolymers in various shapes, including linear polymers, stars blocked stars and glycopolymer self-assemblies were obtained. The bioactivity of these glycopolymers were tested using various types of biological quantifying techniques including turbidity assay, precipitation assay and quartz crystal microbalance (QCM) to study the impact of molecular structure of glycopolymers on their bioactivities towards Concanavalin A.