Portland State University. Department of Chemistry
Date of Award
Doctor of Philosophy (Ph.D.) in Chemistry
1 online resource (xi, 175 p.) : ill. (chiefly col.)
Lectin, Multivalency, Perfluorophenyl azide, Nanomaterials, Nanostructured materials, Glycoconjugates, Carbohydrates
This dissertation focuses on the synthesis and characterization of glyconanomaterials, as well as their applications in studying carbohydrate-protein interactions. A new and versatile method for coupling underivatized carbohydrates to nanomaterials including gold and silica nanoparticles was developed via the photochemically induced coupling reaction of perfluorophenylazide (PFPA). A wide range of carbohydrates including mono-, oligo- and poly-saccharides were conjugated to the nanoparticles with high yields and efficiency. New analytical methods were developed to determine the binding affinities of glyconanoparticles (GNPs) with lectins; these include fluorescence-based competition assay, dynamic light scattering (DLS) and isothermal titration calorimetry (ITC). Results showed that the multivalent presentation of carbohydrate ligands significantly enhanced the binding affinity of GNPs by several orders of magnitude compared to the free ligands. Systematic studies were carried out to investigate the impact of ligand presentation, i.e., the type and length of spacer linkage, the ligand density and the nanoparticle size on the binding affinity of the resulting glyconanoparticles. We used gold GNPs to study interactions with anti-HIV lectin cyanovirin-N (CV-N), and dye-doped silica nanoparticles for labeling glyans and developing high-throughput screening technique.
Wang, Xin, "Synthesis and Characterization of Glyconanomaterials, and Their Applications in Studying Carbohydrate-Lectin Interactions" (2011). Dissertations and Theses. Paper 626.