Synthesis and Structural Study of ribo-Dioxaphosphorinane-Constrained Nucleic Acid Dinucleotides (ribo-a,ss-D-CNA)

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

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 ICT - Institut de Chimie de Toulouse
3 LISBP - Laboratoire d'Ingénierie des Systèmes Biologiques et des Procédés

With increasing interest in the control of the conformations of nucleic acids to define active riboswitch or siRNA, we present herein our efforts towards the stereocontrolled synthesis and conformational analysis of ribodinucleotides in which a and beta torsional angles are constrained within a dioxaphosphorinane structure (ribo-a,beta-D-CNA). The crystal structure analysis of one a,beta-D-CNA TU dimer demonstrates the absolute stereochemistry of the newly created asymmetric centres. NMR and CD analyses allowed complete assignment and the determination of the torsional angles in the a,beta-D-CNA UU diastereoisomers.

Mots clés: Nucleotides; DNA structures; Strained molecules; Phosphorus heterocycles; Conformation analysis; TORSION ANGLE COMBINATIONS; CONFORMATIONALLY RESTRICTED DINUCLEOTIDE; PROTON-MAGNETIC-RESONANCE; HAMMERHEAD RIBOZYME; CRYSTAL-STRUCTURE; DIASTEREOSELECTIVE SYNTHESIS; IN-LINE; NUCLEOSIDES; ALCOHOLS; ALPHA; BETA-D-CNA

Domaines: Sciences du Vivant [q-bio]

Marie Maturano, Dan-Andrei Catana, Pierre Lavedan, Nathalie Tarrat, Nathalie Saffon, et al.. Synthesis and Structural Study of ribo-Dioxaphosphorinane-Constrained Nucleic Acid Dinucleotides (ribo-a,ss-D-CNA). European Journal of Organic Chemistry, 2012, 4, pp.721 - 730. ⟨10.1002/ejoc.201101353⟩. ⟨hal-01268410⟩