Synthesis of Oligonucleotides Containing 2'-Difluorophosphonylated Thioether Adenosine Derivatives and Study of Their Physicochemical Properties.

Authors

Aurore Ceuninck, Maxime Lefeuvre, Robin Fournier, Rémi Legay, Michael Smietana, Thierry Lequeux, Christelle Dupouy, Emmanuel Pfund

Published in

The Journal of organic chemistry. Jul 10, 2026. Epub Jul 10, 2026.

Abstract

Efficient introduction of a difluorophosphonylated allyl or propyl thioether onto the 2'-position of adenosine is described. Following the preparation of phosphoramidites derived from these compounds, oligonucleotides incorporating these new chemical modifications were prepared successfully using a 12-mer model sequence. UV-melting experiments revealed a significant decrease in the thermal stability of modified RNA/RNA duplexes. In contrast, enzymatic degradation studies showed that the difluoromethylphosphonate group slows down enzymatic degradation while simultaneously increasing lipophilicity.

PMID:
42430648
Bibliographic data and abstract were imported from PubMed on 11 Jul 2026.

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