Cyanuric acid (CA), at riazine heterocycle, is extensively utilized for noncovalent self-assembly.T he association between poly(adenine) and CA into micron-length fibers was ar emarkable observation made by Sleiman and coworkers, who proposed that adenine and CA adopt ah exameric rosette configuration in analogy with previously reported structuresf or CA assemblies. However, recent experimental observations from the Krishnamurthyg roup led to a reevaluationo ft he hexameric rosette model,w herein they have proposed ah ydrogen-bonded helicene model as an alternative. Our molecular dynamics simulations show that the hexad model is indeed unlikely and that this novel noncovalent helicene geometry,w here the adenine and CA bases form an extended helical hydrogen-bond network across the system,i samore probable structural motif. The existence of noncovalent helicene compounds may have wide-ranging applicationsi nD NA nanotechnology and helicene chemistry.
The cyanurica cid (CA) heterocycle forms supramolecular structures with adenine nucleobases/nucleosides and oligonucleotides,l eading to speculation that they can act as forerunners to RNA. Herein, the assembly behavior of RNA containing CA and CA-ribose nucleoside was studied. Contrary to previous reports, CA in RNA and the CA-ribonucleoside resulted in destabilization of supramolecular assemblies, which led to ar eevaluation of the CA-adenine hexameric rosette structure. An unprecedented noncovalent supramolecular helicene structure is proposed to account for the striking difference in behavior,which has implications for novel paradigms for reorganizing the structures of nucleic acids, the synthesis of long helicenes, and pre-RNA world paradigms. The results caution against extrapolating the self-assembly behavior of individual heterocycles from the level of monomers to oligomers because the baseparing properties of (non-)canonical nucleobases are impacted by the type of oligomeric backbone to which they are attached.
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