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 46 条
  • [21] RNAHelix: computational modeling of nucleic acid structures with Watson-Crick and non-canonical base pairs
    Bhattacharyya, Dhananjay
    Halder, Sukanya
    Basu, Sankar
    Mukherjee, Debasish
    Kumar, Prasun
    Bansal, Manju
    JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2017, 31 (02) : 219 - 235
  • [22] DFT Investigation of the Interaction of Gold Nanoclusters with Nucleic Acid Base Guanine and the Watson-Crick Guanine-Cytosine Base Pair
    Shukla, Manoj K.
    Dubey, Madan
    Zakar, Eugene
    Leszczynski, Jerzy
    JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (10): : 3960 - 3966
  • [23] Light-emitting self-assembled peptide nucleic acids exhibit both stacking interactions and Watson-Crick base pairing
    Berger, Or
    Adler-Abramovich, Lihi
    Levy-Sakin, Michal
    Grunwald, Assaf
    Liebes-Peer, Yael
    Bachar, Mor
    Buzhansky, Ludmila
    Mossou, Estelle
    Forsyth, V. Trevor
    Schwartz, Tal
    Ebenstein, Yuval
    Frolow, Felix
    Shimon, Linda J. W.
    Patolsky, Fernando
    Gazit, Ehud
    NATURE NANOTECHNOLOGY, 2015, 10 (04) : 353 - 360
  • [24] Interactions of the Watson-Crick nucleic acid base pairs with carbon nanotubes and graphene: DFT and MP2 study
    Stepanian, S. G.
    Karachevtsev, M. V.
    Karachevtsev, V. A.
    Adamowicz, L.
    CHEMICAL PHYSICS LETTERS, 2014, 610 : 186 - 191
  • [25] Hydrogen-bond-mediated photoinduced electron-transfer: Novel dimethylaniline-anthracene ensembles formed via Watson-Crick base-pairing
    Sessler, JL
    Sathiosatham, M
    Brown, CT
    Rhodes, TA
    Wiederrecht, G
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) : 3655 - 3660
  • [26] Watson-Crick Base Pairing of N-Methoxy-1,3-Oxazinane (MOANA) Nucleoside Analogues within Double-Helical DNA
    Afari, Mark N. K.
    Nurmi, Kasper
    Virta, Pasi
    Lonnberg, Tuomas
    CHEMISTRYOPEN, 2023, 12 (07)
  • [27] NMR INVESTIGATION OF ECHINOMYCIN BINDING TO D(ACGTTAACGT)(2) - HOOGSTEEN VERSUS WATSON-CRICK A-CENTER-DOT-T BASE-PAIRING BETWEEN ECHINOMYCIN BINDING-SITES
    PARK, JY
    CHOI, BS
    JOURNAL OF BIOCHEMISTRY, 1995, 118 (05): : 989 - 995
  • [28] The study of the stability of Watson-Crick nucleic acid base pairs in water and dimethyl sulfoxide: Computer simulation by the Monte Carlo method
    Danilov, VI
    Zheltovsky, NV
    Slyusarchuk, ON
    Poltev, VI
    Alderfer, JL
    JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1997, 15 (01): : 69 - 80
  • [29] Crystallographic studies on damaged DNAsIV.: N4-methoxycytosine shows a second face for Watson-Crick base-pairing, leading to purine transition mutagenesis
    Hossain, MT
    Sunami, T
    Tsunoda, M
    Hikima, T
    Chatake, T
    Ueno, Y
    Matsuda, A
    Takénaka, A
    NUCLEIC ACIDS RESEARCH, 2001, 29 (19) : 3949 - 3954
  • [30] BASE-PAIRING OF CYTOSINE ANALOGS WITH ADENINE AND GUANINE IN OLIGONUCLEOTIDE DUPLEXES - EVIDENCE FOR EXCHANGE BETWEEN WATSON-CRICK AND WOBBLE BASE-PAIRS USING H-1-NMR SPECTROSCOPY
    NEDDERMAN, ANR
    STONE, MJ
    LIN, PKT
    BROWN, DM
    WILLIAMS, DH
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (19) : 1357 - 1359