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Reaction of HO . with Guanine Derivatives in Aqueous Solution: Formation of Two Different Redox‐Active OH‐Adduct Radicals and Their Unimolecular Transformation Reactions. Properties of G(‐H) .
Author(s) -
Candeias Luis P.,
Steenken Steen
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000204)6:3<475::aid-chem475>3.0.co;2-e
Subject(s) - chemistry , adduct , deprotonation , oxidizing agent , medicinal chemistry , reactivity (psychology) , radical , aqueous solution , photochemistry , redox , radical ion , oxygen , inorganic chemistry , organic chemistry , medicine , ion , alternative medicine , pathology
The reaction of . OH with 2′‐deoxyguanosine yields two transient species G4 . ‐OH and G8 . ‐OH, which have strongly different reactivity towards O 2 or other oxidants or to reductants. G8 . ‐OH reacts with oxygen with k =4×10 9 M −1 s −1 ; in the absence of oxygen it undergoes a rapid ring‐opening reaction ( k =2×10 5 s −1 ; see scheme). Both G8 . ‐OH and its ring‐opened successor are one‐electron reductants. In contrast, G4 . ‐OH has oxidizing properties; it undergoes a slower transformation reaction ( k =6×10 3 s −1 ) to produce the even more strongly oxidizing (deprotonated) 2′‐deoxyguanosine radical cation.