A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

被引：132

作者：

Park, T ^{[1
]}

Todd, EM ^{[1
]}

Nakashima, S ^{[1
]}

Zimmerman, SC ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 51期

关键词：

D O I：

10.1021/ja0545517

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.

引用

页码：18133 / 18142

页数：10

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