5',8-Cyclo-2'-deoxyadenosine (cdA) formation by gamma-radiation. Theoretical quantum mechanics study.

Boleslaw T Karwowski; Andre Grand; Jean Cadet

doi:10.18388/abp.2009_2499

5',8-Cyclo-2'-deoxyadenosine (cdA) formation by gamma-radiation. Theoretical quantum mechanics study.

Boleslaw T Karwowski 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;
Andre Grand
Jean Cadet

DOI: https://doi.org/10.18388/abp.2009_2499

Abstract

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.

Published

2009-10-15

Issue

Vol. 56 No. 4 (2009)

Section

Articles

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