TY - JOUR
T1 - Molecular Recognition
T2 - Stacking Interactions Influence Watson‐Crick vs. Hoogsteen Base‐Pairing in a Model for Adenine Receptors
AU - Rebek, Julius
AU - Williams, Kevin
AU - Parris, Kevin
AU - Ballester, Pablo
AU - Jeong, Kyu-Sung
PY - 1987/12
Y1 - 1987/12
N2 - 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. (Figure Presented.)
AB - 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. (Figure Presented.)
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U2 - 10.1002/anie.198712441
DO - 10.1002/anie.198712441
M3 - Article
AN - SCOPUS:0023502078
SN - 1433-7851
VL - 26
SP - 1244
EP - 1245
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 12
ER -