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Issue 28, 2017
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Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

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Abstract

The binding selectivity of structurally simple anion receptors is governed by the Hofmeister series (SO42− > HPO42− > carboxylates ∼ H2PO4 > HCO3 > Cl), and exceptions to this rule are rare and require utilization of structurally sophisticated receptors. In this paper we examined a set of 48 structurally diverse anion receptors, barely one fourth of which exhibit selectivity for chloride over more basic dihydrogen phosphate (H2PO4) or carboxylates (MeCO2 and PhCO2). Searching for regularities in the properties of these mainly macrocyclic-derived receptors across quite systematic changes in structure, combined with analysis of multiple crystal structures, allowed us to identify the crucial structural features that are likely required for the occurrence of the phenomenon of selective chloride binding. Examination of a subset of other ‘case study’ receptors reported in the literature as being particularly chloride-selective served as a confirmation of our hypotheses. As such, our findings are valid for all artificial receptors with exceptional selectivity for chloride, as well as for natural chloride channel proteins (ClC).

Graphical abstract: Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

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Publication details

The article was received on 07 Jun 2017, accepted on 23 Jun 2017 and first published on 23 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01385J
Citation: Org. Biomol. Chem., 2017,15, 5927-5943
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    Catching the chloride: searching for non-Hofmeister selectivity behavior in systematically varied polyamide macrocyclic receptors

    K. Dabrowa, F. Ulatowski, D. Lichosyt and J. Jurczak, Org. Biomol. Chem., 2017, 15, 5927
    DOI: 10.1039/C7OB01385J

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