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Author

Shelby Cain

Date of Award

2018

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science

Department

Chemistry

Abstract

Reactive oxygen species have the ability to damage DNA, most predominantly at 2'-deoxyguanosine (dG) to form 8-oxo-2'-deoxyguanosine (OdG). Research has shown that this lesion can base pair to both dC and dA, allowing DNA polymerases to incorrectly incorporate dATP opposite a template OdG, leading to mutation. In order to better understand the effects of specific atoms and properties on OdG mutagenicity, analogs that vary from OdG at specific sites can be studied. However, in order to investigate such analogues, they must first be incorporated into DNA using chemical DNA synthesis. Nucleotides used in chemical DNA synthesis require a dimethoxytrityl (DMTr) group off of the 5'-hydroxyl and a phosphoramidite off of the 3'-hydroxyl. This thesis outlines work focused on adding a 5'-DMTr to three different analogs of OdG. The DMTr derivatives were purified with silica gel column chromatography and their structures were confirmed by 1H NMR.

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