A branched, hydrogen-bonded heterodimer: a novel system for achieving high stability and specificity

被引：12

作者：

Bialecki, Jason B. ^{[1
]}

Yuan, Li-Hua ^{[1
]}

Gong, Bing ^{[1
]}

机构：

[1] SUNY Buffalo, SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON | 2007年 / 63卷 / 25期

基金：

美国国家卫生研究院;

关键词：

ASSOCIATION; COMPLEXES;

D O I：

10.1016/j.tet.2007.04.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Presented is a description of the design, synthesis, and characterization of a novel, branched, six hydrogen-bonded heterodimer termed 'trident'. Two branched oligoamide molecules, 1 and 2, with complementary hydrogen-bonding sequences 3( AD) and 3(DA), respectively, were found to form a very stable (Ka >= 9 x 10(6) M-1) heterodimer in chloroform. Confirmation of the high stability of the heterodimer was obtained through 1D and 2D H-1 NMR spectroscopy, thin-layer chromatography (TLC), and vapor pressure osmometry (VPO). The stability of the trident occurs through the cooperative action of six programmed hydrogen-bonding interactions, which are facilitated by the pre-organization of the individual strands through intramolecular hydrogen bonding. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5460 / 5469

页数：10

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