Date of Graduation

12-2016

Document Type

Thesis

Degree Name

Master of Science in Chemistry (MS)

Degree Level

Graduate

Department

Chemistry & Biochemistry

Advisor/Mentor

Shi, Wei

Committee Member

Durham, Bill

Second Committee Member

Allison, Neil T.

Keywords

Pure sciences

Abstract

The Copper CatalyzedAzide-Alkyne1,3-Dipolar Cycloaddition (CuAAC) reaction has unique features that qualify it to be one of the best click reactions. Its applications have been shown in different aspects and for multiple purposes. The oxidative degradation of biological systems (labile proteins and live cells) is, however, generally recognized as the major problem when using this reaction in living systems. Reactive oxidation species can be easily produced in the presence of copper(II), ascorbate and air, and this is the main cause of toxicity. However, the uses of ligands have shown a major impact on reducing copper toxicity, protecting Cu(I) from the redox potential, and increasing the reaction rate. The aim of this study is to synthesize three different water-soluble ligands for evaluation in CuAAC reactions and to see if they can facilitate CuAAC in aqueous systems. These ligands were chosen because of their low cost and the simplicity of the production process. The key finding of this study is that the three different ligands were able to be synthesized from the same starting materials with small alterations to the process. The three ligands were also evaluated in CuAAC reactions, and it was found that the first ligand with –OH achieved higher efficiency in enhancing the reaction rate than the other ligands.

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