Nucleoside recognition by oligophenyl-based synthetic lectins

Bunyarithi Sookcharoenpinyoa, Emmanuel Klein, Chenfeng Ke & Anthony P. Davis*

Supramolecular Chemistry 2013, 25, 650–655


Synthetic lectins are molecules which bind carbohydrates in aqueous solution through preorganised arrangements of apolar and hydrogen bonding units. In principle, this approach may be used to complex other polar molecules in water, and we now report that two synthetic lectins are also effective for nucleoside substrates. The receptors consist of biphenyl- and terphenyl-based apolar surfaces linked by isophthalamide units to form tricyclic cages. Affinities of up to 2 × 104 M− 1 were measured by 1H NMR and confirmed by isothermal titration calorimetry. These systems show excellent selectivity for nucleosides versus anionic nucleotides, as well as good discrimination between different nucleobase residues.