Spiroiminodihydantoin nucleoside formation from 2′-deoxyguanosine oxidation by [18O-labeled] singlet molecular oxygen in aqueous solution
✍ Scribed by Glaucia Regina Martinez; Jean-Luc Ravanat; Jean Cadet; Marisa Helena Gennari de Medeiros; Paolo Di Mascio
- Publisher
- John Wiley and Sons
- Year
- 2007
- Tongue
- English
- Weight
- 312 KB
- Volume
- 42
- Category
- Article
- ISSN
- 1076-5174
- DOI
- 10.1002/jms.1213
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✦ Synopsis
Abstract
The main singlet molecular oxygen (^1^O~2~) oxidation products of free 2′‐deoxyguanosine (dGuo) in aqueous solution were identified as a pair of diastereomeric spiroiminodihydantoin 2′‐deoxyribonucleosides (dSp) together with 8‐oxo‐7,8‐dihydro‐2′‐deoxyguanosine (8‐oxodGuo). In the present work, evidence is provided from ^18^[^1^O~2~] and H~2~^18^O labeling experiments, using HPLC‐ESI‐MS/MS, that the formation of dSp is explained by the addition of water to a reactive quinonoid intermediate, and a second reaction pathway leading to dSp involves ^1^O~2~ oxidation of initially generated 8‐oxodGuo. Copyright © 2007 John Wiley & Sons, Ltd.