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Issue 8, 2019
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Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence

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Abstract

Two tripodal hexa-urea receptors functionalized with aromatic terminal groups are capable of binding choline phosphate (CP). Crystal structures of the host–guest complexes reveal that the zwitterion CP is efficiently encapsulated in the tripodal hosts in a dual-site binding mode. The phosphate tail of CP is coordinated by the urea groups and the quaternary ammonium head is bound in a ‘composite aromatic box’ through cation–π and hydrogen-bonding interactions. Such a partial aromatic binding environment for the Me3N–+ cation mimics that of most enzymes catalyzing the conversion of quaternary ammonium substrates. Moreover, NMR, ESI-MS, and fluorescence studies demonstrate the selective binding and sensing of CP over other competing species such as ADP, ATP, choline and derivatives.

Graphical abstract: Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence

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Supplementary files

Article information


Submitted
29 Sep 2018
Accepted
26 Dec 2018
First published
27 Dec 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 2483-2488
Article type
Edge Article

Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence

W. Zuo, C. Jia, H. Zhang, Y. Zhao, X. Yang and B. Wu, Chem. Sci., 2019, 10, 2483
DOI: 10.1039/C8SC04338H

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