Anti Regiospecificity in the Photosensitized Cycloaddition of 4-Tetrazolouracil Nucleoside.
Fiche publication
Date publication
octobre 2021
Journal
Photochemistry and photobiology
Auteurs
Membres identifiés du Cancéropôle Est :
Pr GUILLAUME Dominique
Tous les auteurs :
Peyrane F, Denhez C, Guillaume D, Clivio P
Lien Pubmed
Résumé
The (2+2) photocycloaddition of natural pyrimidine nucleobases is devoid of regioselectivity. Although modified pyrimidines have been developed to selectively obtain syn cyclobutane isomers, the targeted formation of anti cyclobutane isomers has not been addressed yet. Herein, using NMR analyses and DFT calculations, we demonstrate that the acetone photosensitized excitation of the 4-tetrazolouracil motif in the nucleoside series specifically provides anti cyclobutane photoproducts in 51% yield. In addition, the cis stereomer formation is preferred over the trans cyclobutane formation (71:29).
Référence
Photochem Photobiol. 2021 Oct 16;: