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Issue 3, 2012
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Recognition of primary amines in water by a zinc funnel complex based on calix[6]arene

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Abstract

A water-soluble calix[6]arene-based tris(imidazole) ligand behaves as a highly selective receptor for primary amines in the presence of Zn(II) in water near physiological pH. It represents the first compound of this family of ligands that binds a Zn dication and an organic guest in water, thus giving rise to a stable host–guest adduct in spite of the highly competitive medium. The herein described self-assembly process displays a remarkable set of biomimetic properties. The ternary system (calix/Zn/amine) is formed in a very synergistic and allosteric manner and stabilizes the neutral form of the amino guest with a spectacular pseudo-pKa shift of ca. 7 units. This system constitutes an interesting structural model of metalloenzymes in aqueous solution.

Graphical abstract: Recognition of primary amines in water by a zinc funnel complex based on calix[6]arene

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Supplementary files

Article information


Submitted
29 Sep 2011
Accepted
16 Nov 2011
First published
16 Nov 2011

Chem. Sci., 2012,3, 811-818
Article type
Edge Article

Recognition of primary amines in water by a zinc funnel complex based on calix[6]arene

O. Bistri, B. Colasson and O. Reinaud, Chem. Sci., 2012, 3, 811
DOI: 10.1039/C1SC00738F

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