Diastereoselective Encapsulation of Tartaric Acid by a Helical Aromatic Oligoamide

被引：109

作者：

Ferrand, Yann ^{[1
,3
]}

Kendhale, Amol M. ^{[1
,3
]}

Kauffmann, Brice ^{[1
,3
]}

Grelard, Axelle ^{[1
,3
]}

Marie, Cecile ^{[2
]}

Blot, Virginie ^{[2
]}

Pipelier, Muriel ^{[2
]}

Dubreuil, Didier ^{[2
]}

Huc, Ivan ^{[1
,3
]}

机构：

[1] Univ Bordeaux, Inst Europeen Chim & Biol, CNRS, UMR5248, F-33607 Pessac, France

[2] Univ Nantes, Lab CEISAM, CNRS, UFR Sci & Tech,UMR6230, F-44322 Nantes 3, France

[3] UMS3033, F-33607 Pessac, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 23期

关键词：

RECOGNITION; OLIGOMERS; RECEPTORS; FOLDAMERS;

D O I：

10.1021/ja102794a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A helical aromatic oligoamide foldamer encapsulates tartaric acid with exceptional affinity, selectivity, and diastereoselectivity. The structure of the complex has been elucidated both in solution by NMR spectroscopy and in the solid state by X-ray crystallography, making it possible to rationalize the strong effects observed, particularly the role of hydrogen bonds between the hydroxyl and carboxylic acid groups of tartaric acid and the inner wall of the helically folded capsule, which completely surrounds the guest and insulates it from the solvent.

引用

收藏

页码：7858 / +

页数：3

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