Mechanistic studies in the radical induced DNA strand cleavage - Formationand reactivity of the radical cation intermediate

Citation
R. Glatthar et al., Mechanistic studies in the radical induced DNA strand cleavage - Formationand reactivity of the radical cation intermediate, TETRAHEDRON, 56(25), 2000, pp. 4117-4128
Citations number
58
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
25
Year of publication
2000
Pages
4117 - 4128
Database
ISI
SICI code
0040-4020(20000616)56:25<4117:MSITRI>2.0.ZU;2-J
Abstract
In order to understand the heterolytic cleavage of 4'-DNA radical 1 and the regioselective attack of nucleophiles at the intermediate DNA radical cati on 3, the chemistry of model radical 8 was studied. It turned out that the heterolytic cleavage in water is favored over homolysis because of the effe ctive solvation of the ions 9 and 10. The regioselectivity of the nucleophi lic attack at radical cation 10 can be explained with the valence bond conf iguration mixing (VBCM) model. (C) 2000 Elsevier Science Ltd. All rights re served.