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

A. Daryl Ariawan, James E.A. Webb, Ethan N.W. Howe, Philip A. Gale, Pall Thordarson*, Luke Hunter

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2962-2967
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number14
DOIs
Publication statusPublished - 14 Apr 2017
Externally publishedYes

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