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

doi:10.1021/ja00020a027

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 (K_a≈ 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 language	English (US)
Pages (from-to)	7640-7645
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	113
Issue number	20
DOIs	https://doi.org/10.1021/ja00020a027
State	Published - Sep 1 1991

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00020a027

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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.",

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AU - Van Engen, Donna

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

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