Design, synthesis and binding properties of conformer-independent linear ADA hydrogen-bonding arrays

The design, synthesis and binding studies of a new class of conformer-independent ADA linear hydrogen-bonding array is described. These phenylureidopyrimidine arrays are shown to adopt the hydrogen-bond pre-organised ADA arrangement by X-ray crystallography and 1H NMR experiments. They bind to complementary DAD arrays with moderate Ka ∼ 56M-1 affinity in a conformer-independent fashion as exemplified by 1H NMR titration and 1H-1H NOESY. The design, synthesis and binding studies of a new class of conformer-independent ADA linear hydrogen-bonding array is described. These phenylureidopyrimidine (PUPY) arrays adopt a hydrogen-bond pre-organised ADA and bind to complementary DAD arrays with Ka ∼ 56M-1.