Dioxaphosphorinane-Constrained Nucleic Acid Dinucleotides as Tools for Structural Tuning of Nucleic Acids

Dan-Andrei Catana (1) , Brice-Loïc Renard (1) , Marie Maturano (1) , Corinne Payrastre (1) , Nathalie Tarrat (2) , Jean-Marc Escudier (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 CEMES-SINanO - Surfaces, Interfaces et Nano-Objets

We describe a rational approach devoted to modulate the sugar-phosphate backbone geometry of nucleic acids. Constraints were generated by connecting one oxygen of the phosphate group to a carbon of the sugar moiety. The so-called dioxaphosphorinane rings were introduced at key positions along the sugar-phosphate backbone allowing the control of the six-torsion angles to ζ defining the polymer structure. The syntheses of all the members of the D-CNA family are described, and we emphasize the effect on secondary structure stabilization of a couple of diastereoisomers of a,b -D-CNA exhibiting wether B-type canonical values or not.

Domaines: Chimie-Physique [physics.chem-ph]

Dan-Andrei Catana, Brice-Loïc Renard, Marie Maturano, Corinne Payrastre, Nathalie Tarrat, et al.. Dioxaphosphorinane-Constrained Nucleic Acid Dinucleotides as Tools for Structural Tuning of Nucleic Acids. Journal of Nucleic Acids , 2012, 2012, pp.1 - 17. ⟨10.1155/2012/215876⟩. ⟨hal-01755340⟩