C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level.
Fiche publication
Date publication
février 2018
Journal
The Journal of organic chemistry
Auteurs
Membres identifiés du Cancéropôle Est :
Pr GUILLAUME Dominique
Tous les auteurs :
Moriou C, Da Silva AD, Vianelli Prado MJ, Denhez C, Plashkevych O, Chattopadhyaya J, Guillaume D, Clivio P
Lien Pubmed
Résumé
Fluorine configuration at C2' of the bis(2'-fluorothymidine) dinucleotide is demonstrated to drive intramolecular base stacking. 2'-β F-Configuration drastically reduces stacking compared to the 2'-α series. Hence, base stacking emerges as being tunable by the C2'-F stereoconfiguration through dramatic puckering variations scrutinized by NMR and natural bond orbital analysis. Accordingly, 2'-β F-isomer photoreactivity is significantly reduced compared to that of the 2'-α F-isomer.
Référence
J. Org. Chem.. 2018 Feb 16;83(4):2473-2478