Triazole–containing zinc(II)dipicolylamine-functionalised peptides as highly selective pyrophosphate sensors in physiological media

Abstract

A small family of linear bis[zinc(II)dipicolylamine] (bis[Zn(II)-DPA])-functionalised peptidic anion receptors has been prepared where the Zn(II)-DPA binding sites have been installed via either a reductive amination reaction or a copper(I)-catalysed azide-alkyne cycloaddition reaction. The latter reaction connects the Zn(II)-DPA binding site and the peptide backbone through a 1,2,3-triazole linkage. Subsequent anion binding studies using indicator displacement assays were conducted to elucidate the effect of the triazole linker on the anion-binding properties of these novel receptors and it was found that the triazole-containing receptors exhibited stronger affinity and slightly improved selectivity for pyrophosphate over adenosine triphosphate and adenosine diphosphate compared to the analogous receptors which did not bear the triazole linker.