Article Dans Une Revue Organic Letters Année : 2019

Difluorophosphonylated Allylic Ether Moiety as a 2′-Modification of RNA-Type Molecules: Synthesis, Thermal, and Metabolic Studies

Résumé

The first synthesis of oligonucleotides incorporating URF, a uridine modified with a difluorophosphonylated allylic ether onto the 2'-position, is described. Fluorinated homouridylates and miR-342-3p analogues are efficiently prepared. UV-melting experiments and enzymatic degradation studies indicate this new series of fluorinated oligonucleotides exhibit good and thermal metabolic stability as well as an increased lipophilicity. Comparison with oligonucleotides containing 2'- O-allyluridine instead of URF reveals improvement of these chemical properties is related to the presence of the difluoromethylphosphonate group.

Domaines

Fichier non déposé

Dates et versions

hal-02168041 , version 1 (28-06-2019)

Identifiants

Citer

Emmanuel Pfund, Christelle Dupouy, Sonia Rouanet, Rémi Legay, Cyril Lebargy, et al.. Difluorophosphonylated Allylic Ether Moiety as a 2′-Modification of RNA-Type Molecules: Synthesis, Thermal, and Metabolic Studies. Organic Letters, 2019, 21 (12), pp.4803-4807. ⟨10.1021/acs.orglett.9b01689⟩. ⟨hal-02168041⟩
125 Consultations
0 Téléchargements

Altmetric

Partager

  • More