A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition
- 1 December 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (51), 18133-18142
- https://doi.org/10.1021/ja0545517
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 ≈ 5 × 107 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.This publication has 22 references indexed in Scilit:
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