Publication Date

April 2017

Advisor(s)

Erika Taylor

Major

Chemistry

Language

English (United States)

Abstract

Trehalose, a compound found in extremophiles such as tardigrades, as well as other organisms, is a disaccharide with stabilizing properties which aids in the preservation of proteins under extreme environmental conditions. Trehalose has been found to protect against desiccation, radiation, and osmotic pressure. A widely accepted model proposes that the hydrogen bonding interactions between trehalose and water molecules lead to a decrease in water loss and in protein mobility. Studying the effects that trehalose has on water dynamics through viscosity, absorption spectroscopy, fluorescence emission, and circular dichroism spectroscopy could give insight into the specific mechanism by which the stabilizing effects are attained. Research testing sugar halogenation has suggested that fluorination of certain disaccharides could lead to greater protein affinity. Thus, synthesis of 6,6’-dideoxy-6,6’difluorotrehalose has been conducted to test the impact that fluorination has on the sugar’s protectant capabilities. The synthetic scheme follows a six-step process involving protection, deprotection, and substitution reactions, and analysis of the products is conducted using nuclear magnetic resonance spectroscopy. Future work will involve the synthesis of 4,4’-dideoxy-4,4’difluorotrehalose to investigate the effects that fluorine placement has on the behavior and interactions of the molecule.

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