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Journal of Nucleic Acids
Volume 2012, Article ID 215876, 17 pages
http://dx.doi.org/10.1155/2012/215876
Review Article

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

1Laboratoire de Synthèse et Physicochimie de Molécules d'Intérêt Biologique, CNRS UMR 5068, Université Paul Sabatier, 31062 Toulouse, France
2Université de Toulouse, INSA, UPS, INP, LISBP, 135 Avenue de Rangueil, 31077 Toulouse, France
3INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, 31400 Toulouse, France

Received 1 June 2012; Accepted 2 August 2012

Academic Editor: Eriks Rozners

Copyright © 2012 Dan-Andrei Catana et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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 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 , -D-CNA exhibiting wether B-type canonical values or not.