Design and Synthesis of Multi-cavity Cyclodextrin Hosts
Date
2019-04-18
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Abstract
Cyclodextrins (CDs) are cyclic oligosaccharides made of α-(1→4)-linked D-glucopyranosyl units. They have found widespread utility in host-guest chemistry, drug delivery, artificial enzymes, and biosensors because of their hydrophobic cavities, which can be used to form inclusion complexes with different organic compounds. Covalently linking CD monomers together in a pre-defined geometry constitutes an attractive strategy to form structurally well-defined multi-cavity hosts. Such novel hosts are expected to have enhanced inclusion capability and furthermore, when interacting with guest molecules of complementary geometry and sizes, the CD cavities can work together, creating the much desired cooperativity effect. In this thesis work, the design and synthesis of two families of multi-cavity CD hosts are reported. Chapter two and three are concerned with the design, synthesis and characterizations of two families of multi-cavity CD hosts. The first family consists of linear hetero-trimers of CDs and the second family includes oligomeric CD hosts linked in a macrocyclic fashion. All these multi-cavity hosts were synthesized using partially O-methylated α-, β- and γ-CDs as building blocks. The highly-efficient copper(I)-catalyzed alkyne/azide 1,3-dipolar cycloaddition reaction was used in all syntheses that shows unparalleled efficiencies. Some initial attempts to characterize the inclusion complexes using isothermal titration calorimetry are also reported in Chapter four, but encountered some difficulties. Finally, the experimental procedures are included in Chapter five.
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Cyclodextrin
Citation
Zhang, Z. (2019). Design and synthesis of multi-cavity cyclodextrin hosts (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.