Common and Potentially Prebiotic Origin for Precursors of Nucleotide Synthesis and Activation

Albert C. Fahrenbach, Constantin Giurgiu, Chun Pong Tam, Li Li, Yayoi Hongo, Masashi Aono, Jack W. Szostak

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)


We have recently shown that 2-aminoimidazole is a superior nucleotide activating group for nonenzymatic RNA copying. Here we describe a prebiotic synthesis of 2-aminoimidazole that shares a common mechanistic pathway with that of 2-aminooxazole, a previously described key intermediate in prebiotic nucleotide synthesis. In the presence of glycolaldehyde, cyanamide, phosphate and ammonium ion, both 2-aminoimidazole and 2-aminooxazole are produced, with higher concentrations of ammonium ion and acidic pH favoring the former. Given a 1:1 mixture of 2-aminoimidazole and 2-aminooxazole, glyceraldehyde preferentially reacts and cyclizes with the latter, forming a mixture of pentose aminooxazolines, and leaving free 2-aminoimidazole available for nucleotide activation. The common synthetic origin of 2-aminoimidazole and 2-aminooxazole and their distinct reactivities are suggestive of a reaction network that could lead to both the synthesis of RNA monomers and to their subsequent chemical activation.

Original languageEnglish
Pages (from-to)8780-8783
Number of pages4
JournalJournal of the American Chemical Society
Issue number26
Publication statusPublished - 2017 Jul 5

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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