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In this thesis, trehalose-based glycopolymers were generated by reversible addition-fragmentation chain transfer polymerization and explored for its applications in infection treatment. Firstly, trehalose-functionalized gold nanoparticles, alongside two glucose-functionalized gold nanoparticles were synthesized and employed in the Staphylococcus aureus (S. aureus) - Human Umbilical Vein Endothelial Cell (HUVEC) infection system. Trehalose-functionalized gold nanoparticles exhibited stronger binding affinity to S. aureus, resulting in impressive inhibition of S. aureus infection towards HUVECs. This result showed promise for the significance of trehalose in anti-adhesion treatment. Secondly, a series of trehalose-based cationic copolymers were synthesized to study the effects of trehalose on antibacterial activity and biocompatibility, in comparison with the neutral hydroxyethyl acrylate. A group of synthesized copolymers successfully showed an activity against S. aureus at concentration in the range of 16 to 64 μg mL-1. The synthesized polymers showed outstanding hemocompatibility. The significance of the polymer chain length, trehalose composition and effects of poly(ethylene glycol) conjugation were evaluated for antibacterial functions and cytotoxicity. The incorporation of trehalose in the polymers improved the selectivity for S. aureus over healthy cells, validating its antibacterial properties. Thirdly, trehalose polymer grafted cellulose nanofibers served as a model nanocarrier system that successfully delivered an antimicrobial drug, ciprofloxacin. This delivery system displayed good dispersibility in aqueous solution and effective antibacterial activity, providing preliminary knowledge to develop trehalose-functionalized drug delivery systems. Overall, these results present a novel application of trehalose-based glycopolymers in infection treatments.