Diastereoselective synthesis of a conformationally restricted dinucleotide with predefined alpha and beta torsional angles for the construction of alpha,beta-constrained nucleic acids (alpha,beta-CNA).
[reaction: see text] The synthesis of a diastereopure 1,3,2-dioxaphosphorinane linkage in which two, alpha and beta, out of six torsion angles of the natural phosphodiester backbone are constrained with predefined values of ca. +60 degrees (g(+)) and 180 degrees (t), respectively, is described. The stable and unstrained six-membered cyclic phosphotriester structure represents the smallest possible ring allowing the conformational locking of the alpha torsion angle at a significant positive value that is typical of many bulged regions of nucleic acids.
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.
Escudier
Jean-Marc
JM
Vigroux
Alain
A
D015226:Dinucleoside Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry; D013237:Stereoisomerism
D015226:Dinucleoside Phosphates; D009696:Nucleic Acids; D010755:Organophosphates