HYDROGEN-BONDING AND MOLECULAR RECOGNITION - SYNTHETIC, COMPLEXATION, AND STRUCTURAL STUDIES ON BARBITURATE BINDING TO AN ARTIFICIAL RECEPTOR

被引：263

作者：

CHANG, SK ^{[1
]}

VANENGEN, D ^{[1
]}

FAN, E ^{[1
]}

HAMILTON, AD ^{[1
]}

机构：

[1] PRINCETON UNIV,DEPT CHEM,PRINCETON,NJ 08544

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 20期

关键词：

D O I：

10.1021/ja00020a027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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, H-1 NMR spectroscopic, and substrate binding studies confirm that six hydrogen bonds are formed between the receptor and its substrate. The strongest binding (K(a) almost-equal-to 10(5) 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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页码：7640 / 7645

页数：6

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