Dioxaphosphorinane-constrained nucleic acid dinucleotides as tools for structural tuning of nucleic acids

Abstract

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 α 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 α, β -D-CNA exhibiting wether B-type canonical values or not. © 2012 Dan-Andrei Catana et al.