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Issue 36, 2017
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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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Supplementary files

Article information


Submitted
22 Mar 2017
Accepted
05 Apr 2017
First published
05 Apr 2017

This article is Open Access

Chem. Commun., 2017,53, 4919-4921
Article type
Communication

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

C. Fernández-García, N. M. Grefenstette and M. W. Powner, Chem. Commun., 2017, 53, 4919
DOI: 10.1039/C7CC02183F

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