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Updated: Mar 6, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate
A Daryl Ariawan1, James E A Webb2, Ethan N W Howe3
1School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia. p.thordarson@unsw.edu.au l.hunter@unsw.edu.au.
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.
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