Guanine Oxidation by Electron Transfer: One‐ versus Two‐Electron Oxidation Mechanism | Zendy

Kupan Adam | Zendy; Saulière Aude | Zendy; Broussy Sylvain | Zendy; Seguy Christel | Zendy; Pratviel Geneviève | Zendy; Meunier Bernard | Zendy

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Guanine Oxidation by Electron Transfer: One‐ versus Two‐Electron Oxidation Mechanism

Author(s) -

Kupan Adam,

Saulière Aude,

Broussy Sylvain,

Seguy Christel,

Pratviel Geneviève,

Meunier Bernard

Publication year - 2006

Publication title -

chembiochem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.05

H-Index - 126

eISSN - 1439-7633

pISSN - 1439-4227

DOI - 10.1002/cbic.200500284

Subject(s) - guanine , chemistry , electron transfer , photochemistry , hydroxymethyl , oligonucleotide , adduct , dna oxidation , radical ion , tris , dna , stereochemistry , organic chemistry , nucleotide , ion , dna damage , biochemistry , gene

The degeneracy of the guanine radical cation, which is formed in DNA by oxidation of guanine by electron transfer, was studied by a detailed analysis of the oxidation products of guanine on oligonucleotide duplexes and by labeling experiments. It was shown that imidazolone, the major product of guanine oxidation, is formed through a one‐electron oxidation process and incorporates one oxygen atom from O 2 . The formation of 8‐oxo‐7,8‐dihydroguanine by a two‐electron oxidation process was a minor pathway. The two‐electron oxidation mechanism was also evidenced by the formation of a tris(hydroxymethyl)aminomethane adduct.

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