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

研究成果: Article査読

50 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)8780-8783
ページ数4
ジャーナルJournal of the American Chemical Society
139
26
DOI
出版ステータスPublished - 2017 7月 5

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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