5',8-Cyclo-2'-deoxyadenosine (cdA) formation by gamma-radiation. Theoretical quantum mechanics study.
Reactions of reactive oxygen species and more specifically - of hydroxyl radical ((*)OH) - with nucleosides may lead to the generation of radicals in the base and 2-deoxyribose moieties. In the present study emphasis was put on the possible reaction modes of 2'-deoxyadenosine (dA) radicals, leading to the formation of related 5',8-cyclonucleosides. It appears that the prerequisite for the formation of 5',8-cyclo-2'-deoxyadenosine (cdA) is the adoption of O4'-exo conformation by 2-deoxyribose; however, this is the least energetically favored conformer among the different puckered forms adopted by the furanose ring. The O4'-exo conformation was found to be present in each of the discussed mechanisms.
Karwowski
Boleslaw T
BT
Laboratoire des Lésions des Acides Nucléiques, INAC/SCIB-UMR-E n degrees 3 CEA-UJF, CEA/Grenoble, Grenoble Cedex 9, France. Bolek.Karwowski@wp.pl
Grand
Andre
A
Cadet
Jean
J
D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000528:radiation effects*; D005720:Gamma Rays; D017665:Hydroxyl Radical / Q000737:chemistry; D008968:Molecular Conformation; D011789:Quantum Theory; D013816:Thermodynamics
D003839:Deoxyadenosines; C056752:8,5'-cyclo-2'-deoxyadenosine; D017665:Hydroxyl Radical; C058118:2'-deoxyadenosine