Hydrogen bonding and molecular recognition: Synthetic, complexation, and structural studies on barbiturate binding to an artificial receptor

Suk Kyu Chang, Andrew Hamilton, Erkang Fan, Andrew D. Hamilton

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 group 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
StatePublished - 1991

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Artificial Receptors
Molecular recognition
Hydrogen Bonding
Complexation
Hydrogen bonds
Substrates
Hydrogen
Binding Sites
X-Rays
Acids
Binding sites
Pharmaceutical Preparations
Nuclear magnetic resonance
X rays
barbituric acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hydrogen bonding and molecular recognition : Synthetic, complexation, and structural studies on barbiturate binding to an artificial receptor. / Chang, Suk Kyu; Hamilton, Andrew; Fan, Erkang; Hamilton, Andrew D.

In: Journal of the American Chemical Society, Vol. 113, No. 20, 1991, p. 7640-7645.

Research output: Contribution to journalArticle

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