title: The 7-nitroindole nucleoside as a photochemical precursor of 2'-deoxyribonolactone: access to DNA fragments containing this oxidative abasic lesion.
abstract: On the basis of molecular modeling studies, the 7-nitroindole nucleoside 1 was selected as a suitable photochemical precursor for photochemical generation of the C1' deoxyribosyl radical under irradiation, which led to 2'-deoxyribonolactone. The nitro-indole nucleoside derivatives 1a and 1b were prepared and their conformation was determined by X-ray crystallography and NMR spectroscopy. The photoreaction of these nucleosides gave the corresponding deoxyribonolactone derivatives efficiently, with release of 7-nitrosoindole. This reaction was successfully applied to synthesis of oligonucleotides containing the deoxyribonolactone lesion.
authors: LEDSS, Chimie Bioorganique, UMR CNRS 5616, Université Joseph Fourier, Grenoble, France. mitsu.kotera@ujf-grenoble.fr
authors: M
authors: M
authors: Kotera
authors: Y
authors: Y
authors: Roupioz
authors: E
authors: E
authors: Defrancq
authors: A G
authors: AG
authors: Bourdat
authors: J
authors: J
authors: Garcia
authors: C
authors: C
authors: Coulombeau
authors: J
authors: J
authors: Lhomme