Watson-Crick base-pairing properties of nucleic acid analogues with stereocontrolled a and torsion angles (α,β-D-CNAs)

被引:37
作者
Dupouy, Christelle [1 ]
Iche-Tarrat, Nathalie [1 ]
Durrieu, Marie-Pierre [1 ]
Rodriguez, Frederic [1 ]
Escudier, Jean-Marc [1 ]
Vigroux, Alain [1 ]
机构
[1] Univ Toulouse 3, CNRS, UMR 5068, Lab Synth & Physicochim Mol Interet Biol, F-31062 Toulouse 9, France
关键词
conformation analysis; DNA structures; helical structures; nucleic acids; oligonucleoticles;
D O I
10.1002/anie.200504475
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Constrained nucleic acids (α,β-D-CNAs) have an ethylene bridge that locks the α and β backbone torsion angles of DNA in the canonical (gauche(-),trans) conformation, as in B-form DNA (see picture), or in the noncanonical (gauche(+),trans) conformation. Canonical α,β-D-CNAs enhance the duplex-forming ability of oligonucleotides with complementary DNA, while noncanonical α,β-D-CNAs stabilize distorted B-DNA structures. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3623 / 3627
页数:5
相关论文
共 39 条
[21]  
LECLEZIO I, UNPUB
[22]   DNA analogues: From supramolecular principles to biological properties [J].
Leumann, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :841-854
[23]   Bicyclic nucleosides and conformational restriction of oligonucleotides [J].
Meldgaard, M ;
Wengel, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3539-3554
[25]   Synthesis and properties of a novel bridged nucleic acid with a P3′→N5′ phosphoramidate linkage, 5′-amino-2′,4′-BNA [J].
Obika, S ;
Nakagawa, O ;
Hiroto, A ;
Hari, Y ;
Imanishi, T .
CHEMICAL COMMUNICATIONS, 2003, (17) :2202-2203
[26]   LNA: a versatile tool for therapeutics and genomics [J].
Petersen, M ;
Wengel, J .
TRENDS IN BIOTECHNOLOGY, 2003, 21 (02) :74-81
[27]   Fourier transform infrared/vibrational circular dichroism spectroscopy as an informative tool for the investigation of large supramolecular complexes of biological macromolecules [J].
Polyanichko, A ;
Wieser, H .
BIOPOLYMERS, 2005, 78 (06) :329-339
[28]  
Schneider B, 1997, BIOPOLYMERS, V42, P113, DOI 10.1002/(SICI)1097-0282(199707)42:1<113::AID-BIP10>3.0.CO
[29]  
2-O
[30]   Synthesis and properties of oligonucleotides having a phosphorus chiral center by incorporation of conformationally rigid 5′-cyclouridylic acid derivatives [J].
Sekine, M ;
Kurasawa, O ;
Shohda, K ;
Seio, K ;
Wada, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6515-6524