First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism

被引：87

作者：

Sugasaki, A ^{[1
]}

Sugiyasu, K ^{[1
]}

Ikeda, M ^{[1
]}

Takeuchi, M ^{[1
]}

Shinkai, S ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Fukuoka 8128581, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 42期

关键词：

D O I：

10.1021/ja010806e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso-meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides. Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 10(5)-10(6) M-2) with Hill coefficients n of 1.8-2.0, and Lewis(X) series and Lewis(a) series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.

引用

页码：10239 / 10244

页数：6

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