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Molecular Recognition: Stacking Interactions Influence Watson‐Crick vs. Hoogsteen Base‐Pairing in a Model for Adenine Receptors
Author(s) -
Rebek Julius,
Williams Kevin,
Parris Kevin,
Ballester Pablo,
Jeong KyuSung
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198712441
Subject(s) - stacking , pairing , chemistry , base pair , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , base (topology) , face (sociological concept) , crystallography , molecule , physics , mathematics , dna , philosophy , quantum mechanics , biochemistry , organic chemistry , superconductivity , mathematical analysis , linguistics
Despite ideal conformation of the two naphthyl esters 1a, b in the solid state , they do not form any edge‐to‐face associates with 9‐ethyladenine in solution. Rather, as detailed NOE and 2D‐NOESY NMR measurements have shown, face‐to‐face associates such as 2 are preferentially formed by stacking interactions, whereby the nature of the base pairing and the bond strengths can be engineered as desired by variation of the substituents.