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Issue 14, 2017
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Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate

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Abstract

Unguisin A (1) is a marine-derived, GABA-containing cyclic heptapeptide. The biological function of this flexible macrocycle is obscure. Here we show that compound 1 lacks any detectable activity in antimicrobial growth inhibition assays, a result that runs contrary to a previous report. However, we find that 1 functions as a promiscuous host molecule in a variety of anion-binding interactions, with high affinity particularly for phosphate and pyrophosphate. We also show that a series of rigidified, backbone-fluorinated analogues of 1 displays altered affinity for chloride ions.

Graphical abstract: Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate

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Publication details

The article was received on 10 Feb 2017, accepted on 06 Mar 2017 and first published on 07 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00316A
Citation: Org. Biomol. Chem., 2017,15, 2962-2967
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    Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate

    A. Daryl Ariawan, J. E. A. Webb, E. N. W. Howe, P. A. Gale, P. Thordarson and L. Hunter, Org. Biomol. Chem., 2017, 15, 2962
    DOI: 10.1039/C7OB00316A

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