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Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

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Abstract

RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.

Graphical abstract: Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

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Publication details

The article was received on 22 Mar 2017, accepted on 05 Apr 2017 and first published on 05 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC02183F
Citation: Chem. Commun., 2017, Advance Article
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    Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

    C. Fernández-García, N. M. Grefenstette and M. W. Powner, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02183F

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