Synthesis of Phostone-Constrained Nucleic Acid (P-CNA) Dinucleotides Through Intramolecular Arbuzov's Reaction

Dan-Andrei Catana (1) , Marie Maturano (1) , Corinne Payrastre (1) , Pierre Lavedan (2) , Nathalie Tarrat (3) , Jean-Marc Escudier (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 Service commun de Résonance Magnétique Nucléaire - RMN (Toulouse, France)
3 CEMES-SINanO - Surfaces, Interfaces et Nano-Objets

P‐CNAs are dinucleotide building blocks in which the torsional angles α and β of the sugar/phosphate backbone are constrained to non‐canonical values within a cyclic phosphonate structure (phostone) synthesised by diastereoselective intramolecular Arbuzov reaction. The reaction has been improved through the use of microwave activation and addition of lithium bromide.

Mots clés: Nucleotides; Strained molecules; Phosphorus; heterocycles; Conformation analysis; chemistry, organic; chemistry

Mots clés: DNA structures

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

Dan-Andrei Catana, Marie Maturano, Corinne Payrastre, Pierre Lavedan, Nathalie Tarrat, et al.. Synthesis of Phostone-Constrained Nucleic Acid (P-CNA) Dinucleotides Through Intramolecular Arbuzov's Reaction. European Journal of Organic Chemistry, 2011, 2011 (34), pp.6857 - 6863. ⟨10.1002/ejoc.201101061⟩. ⟨hal-01755334⟩