Constrained nucleic acids (CNA). Part 2. Synthesis of conformationally restricted dinucleotide units featuring noncanonical alpha/beta/gamma or delta/epsilon/zeta torsion angle combinations.
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.
Le Clézio
Ingrid
I
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.
Gornitzka
Heinz
H
Escudier
Jean-Marc
JM
Vigroux
Alain
A
D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000737:chemistry*; D013237:Stereoisomerism
D009696:Nucleic Acids; D009711:Nucleotides