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Herein, the assembly behavior of RNA containing CA and CA\u2013ribose nucleoside was studied. Contrary to previous reports, CA in RNA and the CA\u2010ribonucleoside resulted in destabilization of supramolecular assemblies, which led to a reevaluation of the CA\u2013adenine 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\u2010RNA world paradigms. The results caution against extrapolating the self\u2010assembly behavior of individual heterocycles from the level of monomers to oligomers because the base\u2010paring properties of (non\u2010)canonical nucleobases are impacted by the type of oligomeric backbone to which they are attached.<\/jats:p>","DOI":"10.1002\/chem.202004397","type":"journal-article","created":{"date-parts":[[2020,11,11]],"date-time":"2020-11-11T03:26:31Z","timestamp":1605065191000},"page":"4033-4042","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["The Unexpected Base\u2010Pairing Behavior of Cyanuric Acid in RNA and Ribose versus Cyanuric Acid Induced Helicene Assembly of Nucleic Acids: Implications for the Pre\u2010RNA Paradigm"],"prefix":"10.1002","volume":"27","author":[{"given":"Brooke A.","family":"Anderson","sequence":"first","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550 North Torrey Pines Road La Jolla CA 92037 USA"},{"name":"NSF-NASA Center for Chemical Evolution  Atlanta GA 30332 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"K\u00e9vin","family":"Fauch\u00e9","sequence":"additional","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550 North Torrey Pines Road La Jolla CA 92037 USA"},{"name":"NSF-NASA Center for Chemical Evolution  Atlanta GA 30332 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Suneesh C.","family":"Karunakaran","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry Parker H. 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