Supramolecular Assembly of Uridine Monophosphate (UMP) and Thymidine Monophosphate (TMP) with a Dinuclear Copper(II) Receptor

Understanding the
intermolecular interactions between nucleotides
and artificial receptors is crucial to understanding the role of nucleic
acids in living systems. However, direct structural evidence showing
precise interactions and bonding features of a nucleoside monophosphate
(NMP) with a macrocycle-based synthetic molecule has not been provided
so far. Herein, we present two novel crystal structures of uridine
monophosphate (UMP) and thymidine monophosphate (TMP) complexes with
a macrocycle-based dinuclear receptor. Structural characterization
of these complexes reveals that the receptor recognizes UMP through
coordinate–covalent interactions with phosphates and π–π
stackings with nucleobases and TMP through coordinate–covalent
interactions with phosphate groups. Furthermore, the receptor has
been shown to effectively bind nucleoside monophosphates in the order
of GMP > AMP > UMP > TMP > CMP in water at physiological
pH, as investigated
by an indicator displacement assay.