Chemistry Faculty Publications
Document Type
Article
Abstract
Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.
Copyright Statement
Publisher PDF
Repository Citation
Nilov, Denis I.; Komarov, Dmitry Y.; Panov, Maxim S.; Karabaeva, Kanykey E.; Mereshchenko, Andrey S.; Tarnovsky, Alexander N.; and Wilson, R. Marshall, "Oxidation Of Adenosine And Inosine: The Chemistry Of 8-oxo-7,8-dihydropurines, Purine Iminoquinones, And Purine Quinones As Observed By Ultrafast Spectroscopy" (2013). Chemistry Faculty Publications. 120.
https://scholarworks.bgsu.edu/chem_pub/120
Publication Date
3-2013
Publication Title
Journal Of The American Chemical Society
DOI
https://doi.org/10.1021/ja3068148
Start Page No.
3423
End Page No.
3438