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A Reevaluation of the Ambident Reactivity of the Guanine Moiety Towards Hydroxyl Radicals
Author(s) -
Chatgilialoglu Chryssostomos,
D'Angelantonio Mila,
Guerra Maurizio,
Kaloudis Panagiotis,
Mulazzani Quinto G.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805372
Subject(s) - moiety , radical , chemistry , tautomer , reactivity (psychology) , guanosine , hydrogen atom abstraction , photochemistry , guanine , deoxyguanosine , medicinal chemistry , stereochemistry , organic chemistry , medicine , nucleotide , biochemistry , alternative medicine , pathology , adduct , gene
Radically different : Contrary to previous proposals, the main reaction of the HO . radical with guanosine or 2′‐deoxyguanosine is the hydrogen abstraction from the NH 2 moiety to give a guanyl radical. This radical, characterized by a broad band in the visible region (around 610 nm), undergoes tautomerization to the most stable isomer.