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Issue 16, 2014
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Fructose controlled ionophoric activity of a cholate–boronic acid

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Abstract

Wulff-type boronic acids have been shown to act as ionophores at pH 8.2 by transporting Na+ through phospholipid bilayers. A cholate–boronic acid conjugate was synthesised and shown to be an ionophore, although the hydroxyl-lined face of the cholate moiety did not enhance ion transport. Mechanistic studies suggested a carrier mechanism for Na+ transport. The addition of fructose (>5 mM) strongly inhibited ionophoric activity of the cholate–boronic acid conjugate, mirrored by a strong decrease in the ability of this compound to partition into an organic phase. Modelling of the partitioning and ion transport data, using a fructose/boronic acid binding constant measured at pH 8.2, showed a good correlation with the extent of fructose/boronic acid complexation and suggested high polarity fructose/boronic acid complexes are poor ionophores. The sensitivity of ion transport to fructose implies that boronic acid-based antibiotic ionophores with activity modulated by polysaccharides in the surrounding environment may be accessible.

Graphical abstract: Fructose controlled ionophoric activity of a cholate–boronic acid

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Publication details

The article was received on 21 Jan 2014, accepted on 27 Feb 2014 and first published on 27 Feb 2014


Article type: Paper
DOI: 10.1039/C4OB00165F
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Citation: Org. Biomol. Chem., 2014,12, 2576-2583
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    Fructose controlled ionophoric activity of a cholate–boronic acid

    J. R. D. Brown, I. C. Pintre and S. J. Webb, Org. Biomol. Chem., 2014, 12, 2576
    DOI: 10.1039/C4OB00165F

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