Expanding the Hoogsteen edge of 2′-deoxyguanosine:: Consequences for G-quadruplex formation

被引:59
作者
Gubala, V [1 ]
Betancourt, JE [1 ]
Rivera, JM [1 ]
机构
[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA
关键词
D O I
10.1021/ol048013v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and self-assembling properties of 8-aryl-2'-deoxyguanosine derivatives are described. Our studies suggest that a properly placed acetyl group can increase the stability and specificity of the resulting G-quadruplex supramolecules by enhancing noncovalent interactions such as hydrogen bonds and z-stacking.
引用
收藏
页码:4735 / 4738
页数:4
相关论文
共 19 条
  • [1] H-1, NA-23, AND P-31 NMR-STUDIES OF THE SELF-ASSEMBLY OF THE 5'-GUANOSINE MONOPHOSPHATE DIANION IN NEUTRAL AQUEOUS-SOLUTION IN THE PRESENCE OF SODIUM-CATIONS
    BORZO, M
    DETELLIER, C
    LASZLO, P
    PARIS, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) : 1124 - 1134
  • [2] STRUCTURE-DIRECTING PROPERTIES OF NA+ IN THE SOLUTION ORDERING OF GUANOSINE 5'-MONOPHOSPHATE - STOICHIOMETRY OF AGGREGATION, BINDING TO ETHIDIUM, AND MODES OF NA+ COMPLEXATION
    BOUHOUTSOSBROWN, E
    MARSHALL, CL
    PINNAVAIA, TJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) : 6576 - 6584
  • [3] G-quartets 40 years later:: From 5′-GMP to molecular biology and supramolecular chemistry
    Davis, JT
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) : 668 - 698
  • [4] CHEMICAL PROBE FOR GLYCOSIDIC CONFORMATION IN TELOMERIC DNAS
    DIAS, E
    BATTISTE, JL
    WILLIAMSON, JR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) : 4479 - 4480
  • [5] SELF-STRUCTURED GUANOSINE 5'-MONOPHOSPHATE - A C-13 AND H-1 MAGNETIC-RESONANCE STUDY
    FISK, CL
    BECKER, ED
    MILES, HT
    PINNAVAIA, TJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) : 3307 - 3314
  • [6] Supramolecular helices via self-assembly of 8-oxoguanosines
    Giorgi, T
    Lena, S
    Mariani, P
    Cremonini, MA
    Masiero, S
    Pieraccini, S
    Rabe, JP
    Samori, P
    Spada, GP
    Gottarelli, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) : 14741 - 14749
  • [7] A dimeric DNA interface stabilized by stacked A•(G•G•G•G)•A hexads and coordinated monovalent cations
    Kettani, A
    Gorin, A
    Majumdar, A
    Hermann, T
    Skripkin, E
    Zhao, H
    Jones, R
    Patel, DJ
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 2000, 297 (03) : 627 - 644
  • [8] Mezzina E, 2001, CHEM-EUR J, V7, P388
  • [9] POLY 8-BROMOGUANYLIC ACID
    MICHELSON, AM
    MONNY, C
    KAPULER, AM
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1970, 217 (01) : 7 - +
  • [10] CONFORMATIONS OF THE 8-METHYLATED AND UNMETHYLATED RIBOHEXAMER R(CGCGCG)2
    RAO, SN
    KOLLMAN, PA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) : 3048 - 3053