Polyanionic Receptors for Carboxylates in Water.

ABSTRACT

Receptors for carboxylate anions have many possible biomedical applications, including mimicry of the vancomycin group of antibiotics.  However, binding carboxylates in water, the biological solvent, is highly challenging due to the hydrophilicity of these polar anions.  Here we report, for the first time, the recognition of simple carboxylates such as acetate and formate in water by synthetic receptors with charge-neutral binding sites.  The receptors are solubilised by polyanionic side-chains which, remarkably, do not preclude anion binding.  The tricyclic structures feature two identical binding sites linked by polyaromatic bridges, capable of folding into closed, twisted conformations.  This folding is hypothesised to preorganise the structures for anion recognition, mimicking the process which generates many protein binding sites.  The architecture is suitable for elaboration into enclosed structures with potential for selective recognition of biologically relevant carboxylates.