Is O-1(2) alone sufficient for DNA cleavage? Possible involvement of paramagnetic intermediates

Citation
M. Chanon et al., Is O-1(2) alone sufficient for DNA cleavage? Possible involvement of paramagnetic intermediates, RES CHEM IN, 25(7), 1999, pp. 633-644
Citations number
50
Categorie Soggetti
Chemistry
Journal title
RESEARCH ON CHEMICAL INTERMEDIATES
ISSN journal
09226168 → ACNP
Volume
25
Issue
7
Year of publication
1999
Pages
633 - 644
Database
ISI
SICI code
0922-6168(1999)25:7<633:IOASFD>2.0.ZU;2-H
Abstract
It is proposed that singlet dioxygen reacting with guanosine or deoxyguanos ine part of nucleotides does not, by itself, cause DNA cleavage. The strand break originates at the endoperoxide stage whenever this link evolves into a O-centered radical. The O-centered radical is then in a good spatial pos ition to abstract an hydrogen intramolecularly from the ribose or desoxyrib ose part of the nucleotide. The carbon centered radical thus formed on the sugar part may lead to strand break either by a p-scission mechanism or by an homolytically induced solvolysis. High pH could also induce cleavage aft er the endoperoxide stage via a base catalyzed ring chain protomerism.