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

被引:60
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 [J].
BORZO, M ;
DETELLIER, C ;
LASZLO, P ;
PARIS, A .
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 [J].
BOUHOUTSOSBROWN, E ;
MARSHALL, CL ;
PINNAVAIA, TJ .
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 [J].
Davis, JT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) :668-698
[4]   CHEMICAL PROBE FOR GLYCOSIDIC CONFORMATION IN TELOMERIC DNAS [J].
DIAS, E ;
BATTISTE, JL ;
WILLIAMSON, JR .
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 [J].
FISK, CL ;
BECKER, ED ;
MILES, HT ;
PINNAVAIA, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3307-3314
[6]   Supramolecular helices via self-assembly of 8-oxoguanosines [J].
Giorgi, T ;
Lena, S ;
Mariani, P ;
Cremonini, MA ;
Masiero, S ;
Pieraccini, S ;
Rabe, JP ;
Samori, P ;
Spada, GP ;
Gottarelli, G .
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 [J].
Kettani, A ;
Gorin, A ;
Majumdar, A ;
Hermann, T ;
Skripkin, E ;
Zhao, H ;
Jones, R ;
Patel, DJ .
JOURNAL OF MOLECULAR BIOLOGY, 2000, 297 (03) :627-644
[8]  
Mezzina E, 2001, CHEM-EUR J, V7, P388
[9]   POLY 8-BROMOGUANYLIC ACID [J].
MICHELSON, AM ;
MONNY, C ;
KAPULER, AM .
BIOCHIMICA ET BIOPHYSICA ACTA, 1970, 217 (01) :7-+
[10]   CONFORMATIONS OF THE 8-METHYLATED AND UNMETHYLATED RIBOHEXAMER R(CGCGCG)2 [J].
RAO, SN ;
KOLLMAN, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3048-3053