Noncovalent Helicene Structure between Nucleic Acids and Cyanuric Acid

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Computational Chemistry

Background:

• Cyanuric acid (CA) is a triazine heterocycle widely used in noncovalent self-assembly.
• Previous studies proposed a hexameric rosette structure for poly(adenine) and CA assemblies.
• Recent experimental data prompted a reevaluation of this proposed structure.

Purpose of the Study:

• To investigate the structural motif of poly(adenine) and cyanuric acid (CA) fibers.
• To evaluate the validity of the hexameric rosette model versus a proposed helicene model.
• To elucidate the noncovalent interactions driving the self-assembly process.

Main Methods:

• Utilized molecular dynamics simulations.
• Analyzed hydrogen-bonding networks.
• Compared simulation results with experimental observations.

Main Results:

• Molecular dynamics simulations indicate the hexad model is unlikely.
• A novel noncovalent helicene geometry is proposed as a more probable structural motif.
• An extended helical hydrogen-bond network between adenine and CA bases was identified.

Conclusions:

• The noncovalent helicene structure is a more likely motif for poly(adenine)-CA assemblies.
• This finding challenges the previously proposed hexameric rosette model.
• Noncovalent helicene compounds hold potential for DNA nanotechnology and helicene chemistry.