Honors Program
Honors in Chemistry
Date of Award
5-2021
Thesis Professor(s)
Dr. Marina Roginskaya
Thesis Professor Department
Chemistry
Thesis Reader(s)
Dr. Abbas Shilabin
Abstract
8-hydroxyguanine (8-oxoG) is one of the most important products resulting from the oxidation of guanine in DNA. 8-oxoG is known as a biomarker of oxidative stress such as lung cancer. 2,5-diamino-4H-imidazol-4-one (Iz) and its hydrolysis product 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)-amino]-2,5-dihydrooxazol-5-one (Oz) are also important products of oxidation of guanine in DNA. Recently, novel types of dimer intermediates related to 8-oxoG and Iz have been identified in our research lab. Using high performance liquid chromatography (HPLC), LC-MS, and NMR coupled with educated hypotheses, it is possible to identify the products, X1 and X2, resulting from the oxidation of guanine and decipher the mechanisms leading to the products. Gaining a better understanding of these mechanisms could potentially lead to more effective medical treatment of conditions resulting from oxidative stress. X1 and X2 were isolated in large amounts from deoxyguanosine (dGuo) via photochemical oxidation. Subsequent testing included a comparison of the effects of different pH values as well as determination of the lifetimes for the X2 product during hydrolysis and reactions with amines. It was shown from the results that X1 undergoes further oxidation to produce X2.
Publisher
East Tennessee State University
Document Type
Honors Thesis - Open Access
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Recommended Citation
Cutright, Zach, "Reaction Pathways Initiated by One-electron Oxidation of Guanine: Reaction Pathways Leading to Stable End Products" (2021). Undergraduate Honors Theses. Paper 742. https://dc.etsu.edu/honors/742
Copyright
Copyright by the authors.