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Is 1O2 Alone Sufficient for Dna Cleavage? Possible Involvement of Paramagnetic Intermediates

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It is proposed that singlet dioxygen reacting with guanosine or deoxyguanosine 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 position to abstract an hydrogen intramolecularly from the ribose or desoxyribose 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 after the endoperoxide stage via a base catalyzed ring chain protomerism.

Affiliations: 1: Laboratoire AM3, case 561, Faculté des Sciences St. Jérôme, 13397 Marseille cédex 20, FRANCE; 2: Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012, INDIA; 3: School of Chemistry, University of Hyderabad, Hyderabad - 500 046, INDIA


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