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
[1]  
[Anonymous], 1988, ANGEW CHEM, V100, P1041, DOI DOI 10.1002/ANGE.19881000804
[2]   Free energy and structural pathways of base flipping in a DNA GCGC containing sequence [J].
Banavali, NK ;
MacKerell, AD .
JOURNAL OF MOLECULAR BIOLOGY, 2002, 319 (01) :141-160
[3]   Phosphates, DNA, and the search for nonterrean life: A second generation model for genetic molecules [J].
Benner, SA ;
Hutter, D .
BIOORGANIC CHEMISTRY, 2002, 30 (01) :62-80
[4]   OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATES - NMR AND UV SPECTROSCOPIC STUDIES OF RP-RP AND SP-SP METHYLPHOSPHONATE (ME) MODIFIED DUPLEXES OF (D[GGAATTCC])2 [J].
BOWER, M ;
SUMMERS, MF ;
POWELL, C ;
SHINOZUKA, K ;
REGAN, JB ;
ZON, G ;
WILSON, WD .
NUCLEIC ACIDS RESEARCH, 1987, 15 (12) :4915-4930
[5]  
BOWER M, 1986, NUCLEIC ACIDS RES, V14, P7421
[6]   CHEMICAL SYNTHESIS OF DNA AND DNA ANALOGS [J].
CARUTHERS, MH .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (09) :278-284
[7]   ANTISENSE OLIGONUCLEOTIDES [J].
DEMESMAEKER, A ;
HANER, R ;
MARTIN, P ;
MOSER, HE .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :366-374
[8]   The crystal structure of the dimerization initiation site of genomic HIV-1 RNA reveals an extended duplex with two adenine bulges [J].
Ennifar, E ;
Yusupov, M ;
Walter, P ;
Marquet, R ;
Ehresmann, B ;
Ehresmann, C ;
Dumas, P .
STRUCTURE, 1999, 7 (11) :1439-1449
[9]   The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes [J].
Freier, SM ;
Altmann, KH .
NUCLEIC ACIDS RESEARCH, 1997, 25 (22) :4429-4443
[10]   Conformationally restricted carbohydrate-modified nucleic acids and antisense technology [J].
Herdewijn, P .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1999, 1489 (01) :167-179