受限核酸（CNA）。第2部分。具有非经典α/β/γ或δ/ε/ζ扭转角组合的构象受限二核苷酸单元的合成。

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

作者信息

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

机构信息

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.

出版信息

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

DOI:10.1021/jo048136t

PMID:15730280

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.

摘要

已经合成了核酸的四种二核苷酸构建单元，其中六个主链扭转角中的三个包含在二氧磷杂环己烷环结构中（D-CNA家族）：两种非对映异构的α,β,γ-D-CNA{顺式和反式}以及两种非对映异构的δ,ε,ζ-D-CNA{（S(C4')，R(P)）和（S(C4')，S(P)）}。使用核磁共振光谱和X射线晶体学对这些构象受限的二核苷酸进行结构分析表明，这些D-CNA结构元件能够稳定扭转角组合α/β/γ和δ/ε/ζ，这些组合与在典型的A-或B型双链体中通常观察到的组合有显著差异。