The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion
✍ Scribed by Mitsuharu Kotera; Yoann Roupioz; Eric Defrancq; Anne-Gaëlle Bourdat; Julian Garcia; Christian Coulombeau; Jean Lhomme
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 156 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
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 nitroindole nucleoside derivatives 1 a and 1 b were prepared and their conformation was determined by X-ray crystallography and NMR spectroscopy. The photo-reaction 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.