An Aminoisoxazole‐Based Proto‐RNA

Xu, Felix; Wiedemann, Stefan; Feldmann, Jonas; Becker, Sidney und Carell, Thomas (27. November 2023): An Aminoisoxazole‐Based Proto‐RNA. In: ChemistryEurope, Vol. 1, No. 3, e202300057

Abstract

The RNA world hypothesis predicts that life started with the development of replicating and catalytically active RNA, which evolved in a process of molecular evolution to increasingly complex chemical structures. RNA is, however, so complex that it has most likely formed from a precursor (proto-RNA) that was more easily accessible in a prebiotic world. Recently, 3-aminoisoxazoles (IO3) were identified as building blocks that can form under prebiotic conditions and can rearrange to give the nucleoside cytidine (C). The present study shows that the constitutional isomer 5-aminoisoxazole (IO5) can undergo the same reaction to give uridine (U). Both compounds (IO3 and IO5), if embedded in RNA, react selectively to C and U, which are the main pyrimidine nucleosides of the genetic system. Importantly, the stereochemical outcome of the IO5 reaction in RNA depends on the neighboring bases. If they are β-configured RNA nucleosides, the reaction proceeds with high selectivity to give exclusively the β-configured U RNA base (anomeric control).

• Item Type: Journal article
• EU Funded Grant Agreement Number: 741912
• EU Projects: Horizon 2020 > ERC Grants > ERC Advanced Grant > ERC Grant 741912: EPiR - The Chemical Basis of RNA Epigenetics
• Form of publication: Publisher's Version
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 326039064
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 325871075
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 201269156
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 393547839