Date of Award

Winter 2018

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry & Biochemistry

Committee Director

Guijun Wang

Committee Member

Patrick Hatcher

Committee Member

Richard Gregory

Committee Member

Venkat Maruthamuthu

Committee Member

Nancy Xu

Abstract

Low molecular-weight gelators (LMWGs) are a fascinating and interesting class of compounds that can self-assemble and form supramolecular structures in appropriate solvents. The gelators form fibrous networks which entrap the solvent and result in a supramolecular gel. Carbohydrate-derived LMWGs are especially useful since they are more likely to be biocompatible and biodegradable. Dendritic gelators are branch-shaped molecules with precise molecular weight that are between small molecules and polymer gelators. Glycoclusters with sugar moieties at the periphery of the molecules are important classes of bioactive compounds due to the multivalency effect. Lower generation glycoclusters are relatively small branched systems that have defined molecular weight and shape. There should be multivalent interactions between the repeating monomeric building blocks. Macrocyclic compounds play an important role in many research fields including drug development, bioorganic chemistry, and materials sciences. Many glycosylated natural macrocyclic compounds have important therapeutic activities and are privileged scaffolds in drug discovery. Apart from their pharmaceutical properties, sugar containing macrocycles have also found applications as catalysts and ligands or sensors for cation or anion recognition, and in the preparation of functional supramolecular assemblies.

In this research, through copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction, also known as “click” chemistry, we designed, synthesized, and characterized three main classes of sugar triazole derivatives. These include the glycolipids (I), glycoclusters (II) andglycomacrocycle (III). These were prepared using readily available sugars such as D-glucose and N-acetyl-D-glucosamine. The design, synthesis and self-assembling properties of glycolipids/clusters as effective low molecular weight gelators will be discussed in this thesis in Chapter 2 and 3. The applications of these novel molecular systems will be explored. In addition, the efficient synthetic route to build glycomacrocycle and structural analysis of these cyclic compounds will be summarized in Chapter 4.

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DOI

10.25777/qq96-mx45

ISBN

9780438900271

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