Large stabilization of a DNA duplex by the deoxyadenosine derivatives tethering an aromatic hydrocarbon group

被引:32
作者
Nakano, S
Uotani, Y
Nakashima, S
Anno, Y
Fujii, M
Sugimoto, N
机构
[1] Konan Univ, High Technol Res Ctr, Higashinada Ku, Kobe, Hyogo 6588501, Japan
[2] Konan Univ, Fac Sci & Engn, Dept Chem, Higashinada Ku, Kobe, Hyogo 6588501, Japan
[3] Kinki Univ, Kyushu Sch Engn, Iizuka, Fukuoka 8208555, Japan
关键词
D O I
10.1021/ja034465b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5′ end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair. Copyright © 2003 American Chemical Society.
引用
收藏
页码:8086 / 8087
页数:2
相关论文
共 12 条
[1]   Thermodynamic parameters for DNA sequences with dangling ends [J].
Bommarito, S ;
Peyret, N ;
SantaLucia, J .
NUCLEIC ACIDS RESEARCH, 2000, 28 (09) :1929-1934
[2]   Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water [J].
Brunsveld, L ;
Vekemans, JAJM ;
Hirschberg, JHKK ;
Sijbesma, RP ;
Meijer, EW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :4977-4982
[3]   Intercalating nucleic acids containing insertions of 1-O-(1-pyrenylmethyl)glycerol:: stabilisation of dsDNA and discrimination of DNA over RNA [J].
Christensen, UB ;
Pedersen, EB .
NUCLEIC ACIDS RESEARCH, 2002, 30 (22) :4918-4925
[4]   Factors contributing to aromatic stacking in water: Evaluation in the context of DNA [J].
Guckian, KM ;
Schweitzer, BA ;
Ren, RXF ;
Sheils, CJ ;
Tahmassebi, DC ;
Kool, ET .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2213-2222
[5]   Experimental measurement of aromatic stacking affinities in the context of duplex DNA [J].
Guckian, KM ;
Schweitzer, BA ;
Ren, RXF ;
Sheils, CJ ;
Paris, PL ;
Tahmassebi, DC ;
Kool, ET .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8182-8183
[6]   Preorganization of DNA: Design principles for improving nucleic acid recognition by synthetic oligonucleotides [J].
Kool, ET .
CHEMICAL REVIEWS, 1997, 97 (05) :1473-1487
[7]   A highly effective nonpolar isostere of deoxyguanosine: Synthesis, structure, stacking, and base pairing [J].
O'Neill, BM ;
Ratto, JE ;
Good, KL ;
Tahmassebi, DC ;
Helquist, SA ;
Morales, JC ;
Kool, ET .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :5869-5875
[8]   Long RNA dangling end has large energetic contribution to duplex stability [J].
Ohmichi, T ;
Nakano, S ;
Miyoshi, D ;
Sugimoto, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10367-10372
[9]   Improved thermodynamic parameters and helix initiation factor to predict stability of DNA duplexes [J].
Sugimoto, N ;
Nakano, S ;
Yoneyama, M ;
Honda, K .
NUCLEIC ACIDS RESEARCH, 1996, 24 (22) :4501-4505
[10]   SEQUENCE DEPENDENCE FOR THE ENERGETICS OF DANGLING ENDS AND TERMINAL BASE-PAIRS IN RIBONUCLEIC-ACID [J].
SUGIMOTO, N ;
KIERZEK, R ;
TURNER, DH .
BIOCHEMISTRY, 1987, 26 (14) :4554-4558