The 7-nitroindole nucleoside as a photochemical precursor of 2'-deoxyribonolactone: access to DNA fragments containing this oxidative abasic lesion.
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.
Kotera
M
M
LEDSS, Chimie Bioorganique, UMR CNRS 5616, Université Joseph Fourier, Grenoble, France. mitsu.kotera@ujf-grenoble.fr
Roupioz
Y
Y
Defrancq
E
E
Bourdat
A G
AG
Garcia
J
J
Coulombeau
C
C
Lhomme
J
J