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

Hidenori Okamura, Antony Crisp, Sarah Hübner, Sidney Becker, Petra Rovó, Thomas Carell

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)18691-18696
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number51
DOIs
Publication statusPublished - 2019 Dec 16

Keywords

  • base pairing
  • origin of life
  • prebiotic chemistry
  • proto-RNA
  • urea

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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