Proto‐Urea‐RNA (Wöhler RNA) Containing Unusually Stable Urea Nucleosides

The RNA world hypothesis assumes that life on Earth began with nucleotides that formed information‐carrying RNA oligomers able to self‐replicate. Prebiotic reactions leading to the contemporary nucleosides are now known, but their execution often requires specific starting materials and lengthy reac...

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Bibliographic Details
Published in:Angewandte Chemie 2019-12, Vol.131 (51), p.18864-18869
Main Authors: Okamura, Hidenori, Crisp, Antony, Hübner, Sarah, Becker, Sidney, Rovó, Petra, Carell, Thomas
Format: Article
Language:English
Subjects:
Abundance
Base pairs
Basenpaarung
Bifurcations
Chemistry
Earth
Gene sequencing
Harnstoff
Hydrogen bonding
Hydrogen bonds
Nucleosides
Nucleotides
Oligomers
Prebiotics
Proto-RNA
Präbiotische Chemie
Ribonucleic acid
Ribose
RNA
Urea
Ureas
Ursprung des Lebens
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Summary:The RNA world hypothesis assumes that life on Earth began with nucleotides that formed information‐carrying RNA oligomers able to self‐replicate. Prebiotic reactions leading to the contemporary nucleosides are now known, but their execution often requires specific starting materials and lengthy reaction sequences. It was therefore proposed that the RNA world was likely proceeded by a proto‐RNA world constructed from molecules that were likely present on the early Earth in greater abundance. Herein, we show that the prebiotic starting molecules bis‐urea (biuret) and tris‐urea (triuret) are able to directly react with ribose. The urea‐ribosides are remarkably stable because they are held together by a network of intramolecular, bifurcated hydrogen bonds. This even allowed the synthesis of phosphoramidite building blocks and incorporation of the units into RNA. Investigations of the nucleotides’ base‐pairing potential showed that triuret:G RNA base pairs closely resemble U:G wobble base pairs. Based on the probable abundance of urea on the early Earth, we postulate that urea‐containing RNA bases are good candidates for a proto‐RNA world. Die präbiotischen Verbindungen Bisharnstoff (Biuret) und Triharnstoff (Triuret) reagieren direkt mit Ribose. Aufgrund eines Netzwerks aus intramolekularen Wasserstoffbrücken sind diese Harnstoff‐modifizierten Ribosiden erstaunlich stabil, was die Synthese von Phosphoramidit‐Bausteinen und die Einbindung der Einheiten in RNA ermöglicht.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201911746