Cyclic peptide unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate. Issue 14 (15th March 2017)

• Record Type: Journal Article
• Authors: Daryl Ariawan, A.; Webb, James E. A.; Howe, Ethan N. W.; Gale, Philip A.; Thordarson, Pall; Hunter, Luke
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 14(2017)
• Page Start: 2962
• Page End: 2967
• Publication Date: 2017-03-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00316a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Unguisin A (1 ) is a marine-derived, GABA-containing cyclic heptapeptide with a high binding affinity for phosphates. 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 compound1 lacks any detectable activity in antimicrobial growth inhibition assays, a result that runs contrary to a previous report. However, we find that1 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 of1 displays altered affinity for chloride ions.