Molecular Recognition: Stacking Interactions Influence Watson‐Crick vs. Hoogsteen Base‐Pairing in a Model for Adenine Receptors

Julius Rebek, Kevin Williams, Kevin Parris, Pablo Ballester, Kyu-Sung Jeong

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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.)

Original languageEnglish
Pages (from-to)1244-1245
Number of pages2
JournalAngewandte Chemie International Edition in English
Volume26
Issue number12
DOIs
Publication statusPublished - 1987 Jan 1

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Molecular recognition
Adenine
Conformations
Esters
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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Molecular Recognition : Stacking Interactions Influence Watson‐Crick vs. Hoogsteen Base‐Pairing in a Model for Adenine Receptors. / Rebek, Julius; Williams, Kevin; Parris, Kevin; Ballester, Pablo; Jeong, Kyu-Sung.

In: Angewandte Chemie International Edition in English, Vol. 26, No. 12, 01.01.1987, p. 1244-1245.

Research output: Contribution to journalArticle

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