53009-05-5Relevant academic research and scientific papers
Efficient chemical synthesis of oligonucleotides containing the 2- deoxyribonolactone site
Kotera, Mitsuharu,Bourdat, Anne-Gaelle,Defrancq, Eric,Jourdan, Muriel,Garcia, Julian,Coulombeau, Christian,Lhomme, Jean
, p. 1323 - 1324 (1999)
A highly efficient synthetic method for incorporation of the deoxyribonolactone lesion into oligonucleotides was developed using the photochemical properties of 7-nitroindole.
A Convenient Synthesis of Protoanemonin
Crey, Caroline,Dumy, Pascal,Lhomme, Jean,Kotera, Mitsuharu
, p. 3727 - 3732 (2007/10/03)
A new convenient synthesis of protoanemonin (1) starting from 2-deoxy-D-ribose (3) is described. A key step in the sequence is the successive β- and δ-eliminations of 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone (6).
The 7-nitroindole nucleoside as a photochemical precursor of 2′-deoxyribonolactone: Access to DNA fragments containing this oxidative abasic lesion
Kotera, Mitsuharu,Roupioz, Yoann,Defrancq, Eric,Bourdat, Anne-Gaelle,Garcia, Julian,Coulombeau, Christian,Lhomme, Jean
, p. 4163 - 4169 (2007/10/03)
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 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.
