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

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The first synthesis of oligonucleotides incorporating U RF, 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 U RF reveals improvement of these chemical properties is related to the presence of the difluoromethylphosphonate group.