Hydrogen Bonding and Molecular Recognition: Synthetic, Complexation, and Structural Studies on Barbiturate Binding to an Artificial Receptor

Erkang Fan, Andrew D. Hamilton, Suk Kyu Chang, Donna Van Engen

Research output: Contribution to journalArticle

Abstract

A series of synthetic receptors with strong selectivity for the barbiturate family of drugs has been prepared. The receptor design is based on two 2,6-diaminopyridine groups linked through an isophthalic acid spacer. X-ray crystallographic, 1H NMR spectroscopic, and substrate binding studies confirm that six hydrogen bonds are formed between the receptor and its substrate. The strongest binding (Ka≈ 105 M−1) is seen to those substrates containing the complementary barbituric acid core. Systematic deletion of hydrogen-bonding sites from the receptor and substrate allows an assessment of the contribution of individual binding sites to complexation.

Original languageEnglish (US)
Pages (from-to)7640-7645
Number of pages6
JournalJournal of the American Chemical Society
Volume113
Issue number20
DOIs
StatePublished - Sep 1 1991

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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