A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition

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. Th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-12, Vol.127 (51), p.18133-18142
Main Authors: Park, Taiho, Todd, Eric M, Nakashima, Shoji, Zimmerman, Steven C
Format: Article
Language:English
Subjects:
Biological and medical sciences
Crystallography, X-Ray
Fundamental and applied biological sciences. Psychology
Guanosine - analogs & derivatives
Guanosine - chemistry
Hydrogen Bonding
Interactions. Associations
Intermolecular phenomena
Kinetics
Molecular biophysics
Naphthyridines - chemistry
Nuclear Magnetic Resonance, Biomolecular
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Urea - analogs & derivatives
Urea - chemistry
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Summary: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 ≈ 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 (K dimer < 10 M-1) and UG (K dimer ca. 200−300 M-1) means that the UG·DAN complex forms with unparalleled fidelity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0545517