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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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Supplementary files

Article information


Submitted
10 Feb 2017
Accepted
06 Mar 2017
First published
07 Mar 2017

Org. Biomol. Chem., 2017,15, 2962-2967
Article type
Paper

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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