Journal of the American Chemical Society 2005-12-28

A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition.

Taiho Park, Eric M Todd, Shoji Nakashima, Steven C Zimmerman

Index: J. Am. Chem. Soc. 127(51) , 18133-42, (2005)

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Abstract

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 (Kassoc approximately 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 (Kdimer < 10 M(-1)) and UG (Kdimer ca. 200-300 M(-1)) means that the UG.DAN complex forms with unparalleled fidelity.