Formation of RNA Phosphodiester Bond by Histidine-Containing Dipeptides

Rafal D. Wieczorek, Mark Dörr, Agata Chotera, Pier Luigi Luisi, Pierre Alain Monnard

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

A new scenario for prebiotic formation of nucleic acid oligomers is presented. Peptide catalysis is applied to achieve condensation of activated RNA monomers into short RNA chains. As catalysts, L-dipeptides containing a histidine residue, primarily Ser-His, were used. Reactions were carried out in selforganised environment, a water-ice eutectic phase, with low concentrations of reactants. Incubation periods up to 30 days resulted in the formation of short oligomers of RNA. During the oligomerisation, an active intermediate (dipeptide-mononucleotide) is produced, which is the reactive species. Details of the mechanism and kinetics, which were elucidated with a set of control experiments, further establish that the imidazole side chain of a histidine at the carboxyl end of the dipeptide plays a crucial role in the catalysis. These results suggest that this oligomerisation catalysis occurs by a transamination mechanism. Because peptides are much more likely products of spontaneous condensation than nucleotide chains, their potential as catalysts for the formation of RNA is interesting from the origin-of-life perspective. Finally, the formation of the dipeptide-mononucleotide intermediate and its significance for catalysis might also be viewed as the tell-tale signs of a new example of organocatalysis.

Original languageEnglish
Pages (from-to)217-223
Number of pages7
JournalChemBioChem
Volume14
Issue number2
DOIs
StatePublished - 1 Jan 2013
Externally publishedYes

Keywords

  • Catalysts
  • Nucleotides
  • Origin of life
  • Peptides
  • RNA formation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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