In the field of biomedical, there has been a rising interest in designing artificial receptors that recognize nucleotides as target substrates with the goal to mimic their biological interactions with enzymes. Understanding the intermolecular interactions between nucleotides and artificial receptors is important to assess the activities of nucleic acids in living system. However, direct structural evidence showing precise interactions and bonding features of a nucleoside monophosphate (NMP) with a macrocyle-based synthetic receptor has not been provided so far. During this research, a polyamine macrocycle was synthesized by Schif’s base reaction between 2,2’-diamino-<i>N</i>-methyldiethylamine and terephthaladehyde in high dilution condition followed by NaBH<sub>4</sub> reduction. The macrocycle was converted to dinuclear Cu(II) complex and studied for recognition of NMPs. Herein, two novel crystal structures of uridine monophosphate and thymidine monophosphate complexes with a macrocyle-based dinuclear receptor will be presented in detail. Structural characterization of these complexes reveals that the receptor recognizes TMP through coordinate−covalent interaction with a phosphate anion and UMP through coordinate−covalent interaction with a phosphate anion and π−π stacking with a nucleobase. Furthermore, the receptor binds nucleoside monophosphates in the order of GMP &gt; AMP &gt; UMP &gt; TMP &gt; CMP in water at physiological pH, as investigated by an indicator displacement assay.

Supramolecular assembly of uridine monophosphate (UMP) and thymidine monophosphate (TMP) with a dinuclear copper(II) receptor

2019 Fall National Meeting

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