The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

Autor:	Julian Garcia, Anne-Gaëlle Bourdat, Yoann Roupioz, Jean Lhomme, Christian Coulombeau, Eric Defrancq, Mitsuharu Kotera
Rok vydání:	2000
Předmět:	Molecular model Oligonucleotide Organic Chemistry General Chemistry DNA oxidation Nuclear magnetic resonance spectroscopy Oxidative phosphorylation Photochemistry Catalysis Lesion chemistry.chemical_compound chemistry medicine medicine.symptom Nucleoside DNA
Zdroj:	Europe PubMed Central Scopus-Elsevier
ISSN:	1521-3765 0947-6539
DOI:	10.1002/1521-3765(20001117)6:22<4163::aid-chem4163>3.0.co;2-k
Popis:	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 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.
Databáze:	OpenAIRE
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