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Synthetic water soluble di-/tritopic molecular receptors exhibiting Ca2+/Mg2+ exchange

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Abstract

Structural integration of two synthetic water soluble receptors for Ca2+ and Mg2+, namely 1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid (BAPTA) and o-aminophenol-N,N,O-triacetic acid (APTRA), respectively, gave novel di- and tritopic ionophores (1 and 2). As Mg2+ and Ca2+ cannot be simultaneously complexed by the receptors, allosteric control of complexation results. Potentiometric measurements established stepwise protonation constants and showed high affinity for Ca2+ (log K = 6.08 and 8.70 for 1 and 2, respectively) and an excellent selectivity over Mg2+ (log K = 3.70 and 5.60 for 1 and 2, respectively), which is compatible with magnesium–calcium ion exchange. While ion-exchange of a single Mg2+ for a single Ca2+ is possible in both 1 and 2, the simultaneous binding of two Mg2+ by 2 appears prohibitive for replacement of these two ions by a single Ca2+. Ion-binding and exchange was further rationalized by DFT calculations.

Graphical abstract: Synthetic water soluble di-/tritopic molecular receptors exhibiting Ca2+/Mg2+ exchange

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Publication details

The article was received on 14 Dec 2016, accepted on 25 Apr 2017 and first published on 25 Apr 2017


Article type: Paper
DOI: 10.1039/C6OB02732F
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthetic water soluble di-/tritopic molecular receptors exhibiting Ca2+/Mg2+ exchange

    A. Lavie-Cambot, A. Tron, A. Ducrot, F. Castet, B. Kauffmann, L. Beauté, H. Allouchi, J. Pozzo, C. S. Bonnet and N. D. McClenaghan, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C6OB02732F

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