Design and NMR characterization of reversible head-to-tail boronate-linked macrocyclic nucleic acids

Inspired by the ability of boronic acids to bind with compounds containing diol moieties, we envisioned the formation in solution of boronate ester-based macrocycles by the head-to-tail assembly of a nucleosidic precursor that contains both a boronic acid and the natural 2 ',3 '-diol of ribose. DOSY NMR spectroscopy experiments in water and anhydrous DMF revealed the dynamic assembly of this precursor into dimeric and trimeric macrocycles in a concentration-dependent fashion as well as the reversibility of the self-assembly process. NMR experimental values and quantum mechanics calculations provided further insight into the sugar pucker conformation profile of these macrocycles.

Automated summary

Inspired by boronic acids' ability to bind with diol-containing compounds, we successfully formed boronate ester-based macrocycles through assembly in solution, and investigated their dynamic assembly and sugar pucker conformation profile.