Selective enhancement of the one-electron oxidation of guanine by base pairing with cytosine

被引:0
|
作者
Kawai, K [1 ]
Wata, Y [1 ]
Ichinose, N [1 ]
Majima, T [1 ]
机构
[1] Osaka Univ, Inst Sci & Ind Res, SANKEN, Ibaraki, Osaka 5670047, Japan
关键词
D O I
10.1002/1521-3773(20001201)39:23<4327::AID-ANIE4327>3.0.CO;2-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The oxidation potential of guanine is lowered by 100 mV on selective hydrogen bonding to a cytosine residue. This has been established by examining the effects of the base pairing of guanine to other nucleosides on the rate constant of the electron transfer from guanine to the excited electron acceptor molecule N,N'-dibutylnaphthaladiimide (NDI, see scheme). An enhancement of the electron transfer was observed selectively for the G:C pair.
引用
收藏
页码:4327 / +
页数:4
相关论文
共 50 条
  • [1] Regulation of one-electron oxidation rate of guanine by base pairing with cytosine derivatives
    Kawai, K
    Wata, Y
    Hara, M
    Tojo, S
    Majima, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) : 3586 - 3590
  • [2] Effects of base pairing on the one-electron reduction rate of cytosine
    Kawai, K
    Yokoohji, A
    Tojo, S
    Majima, T
    CHEMICAL COMMUNICATIONS, 2003, (22) : 2840 - 2841
  • [3] Theoretical Study of the Tautomerism in the One-Electron Oxidized Guanine-Cytosine Base Pair
    Ceron-Carrasco, J. P.
    Requena, A.
    Perpete, E. A.
    Michaux, C.
    Jacquemin, D.
    JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (42): : 13439 - 13445
  • [4] DFT calculations on the deprotonation site of the one-electron oxidised guanine-cytosine base pair
    Steenken, Steen
    Reynisson, Johannes
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2010, 12 (31) : 9089 - 9094
  • [5] Molecular mechanism of base pairing infidelity during DNA duplication upon one-electron oxidation
    Reynisson, Johannes
    WORLD JOURNAL OF CLINICAL ONCOLOGY, 2010, 1 (01): : 12 - 17
  • [6] One-electron oxidation of DNA: thymine versus guanine reactivity
    Kanvah, Sriram
    Schuster, Gary B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) : 1340 - 1343
  • [7] Effect of Base Pairing on the Electrochemical Oxidation of Guanine
    Costentin, Cyrille
    Hajj, Viviane
    Robert, Marc
    Saveant, Jean-Michel
    Tard, Cedric
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (29) : 10142 - 10147
  • [8] Marked variations of dissociation energy and H-bond character of the guanine-cytosine base pair induced by one-electron oxidation and Li+ cation coupling
    Sun, LX
    Bu, YX
    JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (01): : 593 - 600
  • [9] Excited States of One-Electron Oxidized Guanine-Cytosine Base Pair Radicals: A Time Dependent Density Functional Theory Study
    Kumar, Anil
    Sevilla, Michael D.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2019, 123 (14): : 3098 - 3108
  • [10] Recognition of substituted cytosine derivatives by the base pairing with guanine connected to pyrene
    Kawai, T
    Ikegami, M
    Kawai, K
    Majima, T
    Nishimura, Y
    Arai, T
    CHEMICAL PHYSICS LETTERS, 2005, 407 (1-3) : 58 - 62