The first water-soluble bowl complex: molecular recognition of acetate by the biomimetic tris(imidazole) Zn(II) system at pH 7.4

A supramolecular approach for modeling active sites of metallo-enzymes relies on the association of a metal ion bound to a tris(imidazole) core under the control of a cavity. One step further is the water-solubilization of the cavity-complex. Here, we describe the synthesis of a water-soluble bowl-ligand that has been successively achieved through an 11-step strategy from resorcinol. First insights into its coordination properties in water show that it readily binds Zn(II) at physiological pH and acts as a molecular receptor for the hydrophilic acetate guest ligand.