Non-canonical nucleobases and their respective nucleotides having more than one hydrogen-bonding ‘face’ (e.g., cyanuric acid and 2,4,6-triaminopyrimidine) can spontaneously self-assemble via hydrogen-bonding to form non-covalent higher ordered structures (e.g., hexameric rosettes). Such properties give credence to the ability of alternative nucleobases to function in an RNA-like polymer. To determine if hexad formation is feasible with covalently-linked non-canonical nucleobases and nucleotides, we synthesized RNA oligomers containing cyanuric acid nucleobases. Then, we investigated their base-pairing properties and their ability to self-assemble into hexameric rosette structures. The base-pairing properties of these complex systems were evaluated by thermal stability analysis (Tm), absorbance scans, circular dichroism, polyacrylamide gel electrophoresis, and atomic force microscopy. Such plausibly prebiotic self-assembling structures are of interest in the context of Origin of Life studies. They could give clues as to how the nucleic acid polymers appeared and how they may have evolved into the extant genetic material: RNA and DNA.

Synthesis of cyanuric acid-containing oligonucleotides and their self-assembly properties

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.