Understanding the binding properties of phosphorylated glycoluril-derived molecular tweezers and selective nanomolar binding of natural polyamines in aqueous solution†

A modular synthetic platform for the construction of flexible glycoluril-derived molecular tweezers was developed. The binding properties of four exemplary supramolecular hosts obtained via this approach towards 16 organic amines were investigated by means of H-1 NMR titration. In this work, we compare the K-a values obtained this way with those of three structurally related molecular tweezers and provide a computational approach towards an explanation of the observed behavior of those novel hosts. The results showcase that certain structural modifications lead to very potent and selective binders of natural polyamines, with observed binding of spermine below 10 nM.

Automated summary

A modular synthetic platform for constructing flexible glycoluril-derived molecular tweezers was developed and investigated for their binding properties towards 16 organic amines through H-1 NMR titration. The results demonstrated that certain structural modifications can lead to potent and selective binding of natural polyamines by the molecular tweezers.