Constrained nucleic acids (CNA). Part 2. Synthesis of conformationally restricted dinucleotide units featuring noncanonical alpha/beta/gamma or delta/epsilon/zeta torsion angle combinations

Ingrid Le Clézio; Heinz Gornitzka; Jean-Marc Escudier; Alain Vigroux

doi:10.1021/jo048136t

Constrained nucleic acids (CNA). Part 2. Synthesis of conformationally restricted dinucleotide units featuring noncanonical alpha/beta/gamma or delta/epsilon/zeta torsion angle combinations

J Org Chem. 2005 Mar 4;70(5):1620-9. doi: 10.1021/jo048136t.

Authors

Ingrid Le Clézio¹, Heinz Gornitzka, Jean-Marc Escudier, Alain Vigroux

Affiliation

¹ Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (UMR 5068), Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cedex 4, France.

PMID: 15730280
DOI: 10.1021/jo048136t

Abstract

Four dinucleotide building units of nucleic acids in which three out of six backbone torsion angles are included in a dioxaphosphorinane ring structure (D-CNA family) have been synthesized: two diastereoisomeric alpha,beta,gamma-D-CNA {cis and trans} and two diastereoisomeric delta,epsilon,zeta-D-CNA {(S(C4'),R(P)) and (S(C4'),S(P))}. The structural analysis of these conformationally restricted dinucleotides, using NMR spectroscopy and X-ray crystallography, shows that these D-CNA structural elements allow the stabilization of torsion angle combinations, alpha/beta/gamma and delta/epsilon/zeta, that are significantly different from those typically observed in canonical A- or B-form duplexes.

MeSH terms

Models, Molecular
Nucleic Acid Conformation*
Nucleic Acids / chemical synthesis*
Nucleic Acids / chemistry
Nucleotides / chemistry*
Stereoisomerism

Substances

Nucleic Acids
Nucleotides