Pyrene-labeled deoxyuridine and deoxyadenosine: fluorescent discriminating phenomena in their oligonucleotides

被引:43
作者
Hwang, GT [1 ]
Seo, YJ [1 ]
Kim, BH [1 ]
机构
[1] Pohang Univ Sci & Technol, Div Mol & Life Sci, Dept Chem, Natl Res Lab, Pohang 790784, South Korea
关键词
fluorescence; excimer; interstrand stacking; nucleotides;
D O I
10.1016/j.tetlet.2005.01.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrene-labeled deoxyuridine (U-P) and deoxyadenosine (A(P)) units, which are substituted at the C-5 and C-8 positions, respectively, are fluorescent unnatural nucleosides. When duplexes are formed, these nucleobases feature strong and stable interstrand stacking interactions between the two pyrene units, which compensate for the loss of hydrogen bonding and induce characteristic pyrene excimer emissions. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1475 / 1477
页数:3
相关论文
共 28 条
[1]  
Amann N, 2002, ANGEW CHEM INT EDIT, V41, P2978, DOI 10.1002/1521-3773(20020816)41:16<2978::AID-ANIE2978>3.0.CO
[2]  
2-5
[3]   Polycyclic aromatic DNA-Base surrogates: High-affinity binding to an adenine-specific base-flipping DNA methyltransferase [J].
Beuck, C ;
Singh, I ;
Bhattacharya, A ;
Heckler, W ;
Parmar, VS ;
Seitz, O ;
Weinhold, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3958-3960
[4]   DNA with hydrophobic base substitutes: A stable, zipperlike recognition motif based on interstrand-stacking interactions [J].
Brotschi, C ;
Leumann, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (14) :1655-1658
[5]  
GAIT MJ, 1984, OLIGONUCLEOTIDE SYNT
[6]   Beyond A, C, G and T: augmenting nature's alphabet [J].
Henry, AA ;
Romesberg, FE .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (06) :727-733
[7]   Novel fluorophores: Efficient synthesis and photophysical study [J].
Hwang, GT ;
Son, HS ;
Ku, JK ;
Kim, BH .
ORGANIC LETTERS, 2001, 3 (16) :2469-2471
[8]   Synthesis and photophysical studies of bis-enediynes as tunable fluorophores [J].
Hwang, GT ;
Son, HS ;
Ku, JK ;
Kim, BH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11241-11248
[9]   π-conjugated dendrimers based on bis(enediynyl) benzene units [J].
Hwang, GT ;
Kim, BH .
ORGANIC LETTERS, 2004, 6 (16) :2669-2672
[10]   Fluorescent oligonucleotide incorporating 5-(1-ethynylpyrenyl)2′-deoxyuridine:: sequence-specific fluorescence changes upon duplex formation [J].
Hwang, GT ;
Seo, YJ ;
Kim, SJ ;
Kim, BH .
TETRAHEDRON LETTERS, 2004, 45 (18) :3543-3546