Synthesis and anion-binding properties of new disulfonamide-based receptors

被引：14

作者：

Mammoliti, Oscar ^{[1
]}

Allasia, Sara ^{[1
]}

Dixon, Sally ^{[1
]}

Kilburn, Jeremy D. ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Dept Chem, Southampton SO17 1BJ, Hants, England

来源：

TETRAHEDRON | 2009年 / 65卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

AMINO-ACID RECOGNITION; N-PROTECTED GLUTAMATE; MOLECULAR RECOGNITION; CARBOXYLATE BINDING; GUANIDINIOCARBONYL PYRROLES; COMPLEX STABILITY; SELECTIVE BINDING; OXOANION BINDING; AQUEOUS-SOLUTION; SOLID-STATE;

D O I：

10.1016/j.tet.2009.01.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d(3) with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. L-Valine derived macrocycles maintain tight 1:1 binding of acetate (K-a(1:1) >10(4) M-1) in MeCN-d(3) and display preference for oxyanion binding in more competitive MeCN-d(3)/2% H2O. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2184 / 2195

页数：12

共 73 条

[1] Supramolecular control for the modular synthesis of pseudopeptidic macrocycles through an anion-templated reaction [J].