Type of Document Dissertation Author Kaur, Gurpreet Author's Email Address gurpreetk08@gmail.com URN etd-11292006-161029 Title Synthesis of Boronic Acid Based Sensors for Glucose and Sialic Acid and Synthesis of Novel and Selective PDE4 Enzyme Inhibitors Degree Ph.D. Department Chemistry Advisory Committee
Advisor Name Title Binghe Wang Committee Chair David Boykin Committee Member Shahab Shamsi Committee Member Keywords
- glucose sensors
- sialic acid sensors
- enzyme inhibitors
- PDE4
- Boronic acid
- fluorescence
Date of Defense 2006-09-27 Availability unrestricted Abstract The boronic acid functional group is known to bind compounds with the diol group tightly and reversibly in aqueous environment and has been used as a recognition moiety for the design of carbohydrate sensors. The first chapter of the dissertation studies the synthesis and substitution effect on the affinity and selectivity of a known boronic acid-based glucose sensor. In such a sensor design effort, the availability of a signaling event, whether it is fluorescence or UV, is crucial. The second chapter studies the detailed mechanism on how a well-known fluorescent boronic acid compound changes fluorescent properties upon binding. A new mechanism has been established which corrected a decade old mistake. In the third chapter, a series of boronic acid-based sensors were designed and synthesized for sialic acid, which is part of tetrasaccharide found on many cell surface carbohydrates. Such sialic acid sensors could be very useful for the development of new type of anti-influenza therapy. The fourth is on the design and synthesis novel and selective inhibitors for phosphodiesterase 4 (PDE4), which are potential anti-asthma agents.Files
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