A C3′ modified nucleotide. The difluorophosphonate function, a phosphate mimic, governs the conformational behaviour of the ribofuranose

Catherine Fressigné (1) , Serge Piettre (1) , Eric Condamine (1) , Cornelis Altona (2) , Arnaud Gautier (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Leiden Institute of Chemistry

A conformational analysis using the Pseurot 6.3 software package of a modified nucleoside-3′-phosphate is reported and reveals that the phosphate mimic strongly influences the conformational behaviour of the ribose ring and shifts the North/ South equilibrium to a northern position. A rational classification by the group electronegativity of several phosphate analogues is presented. The λ factor of the difluorophosphonate group in water (Diez–Donders generalised Karplus equation) is also determined.

Domains: Chemical Sciences

Catherine Fressigné, Serge Piettre, Eric Condamine, Cornelis Altona, Arnaud Gautier. A C3′ modified nucleotide. The difluorophosphonate function, a phosphate mimic, governs the conformational behaviour of the ribofuranose. Tetrahedron, 2005, 61 (20), pp.4769-4777. ⟨10.1016/j.tet.2005.03.028⟩. ⟨hal-02357629⟩