title: Prebiotic synthesis of aminooxazoline-5'-phosphates in water by oxidative phosphorylation.
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.
authors.affiliation: Department of Chemistry, UCL, 20 Gordon St., London, WC1H 0AJ, UK. matthew.powner@ucl.ac.uk.
authors.forename: C
authors.initials: C
authors.lastname: Fernández-García
authors.affiliation: Department of Chemistry, UCL, 20 Gordon St., London, WC1H 0AJ, UK. matthew.powner@ucl.ac.uk.
authors.forename: N M
authors.initials: NM
authors.lastname: Grefenstette
authors.affiliation: Department of Chemistry, UCL, 20 Gordon St., London, WC1H 0AJ, UK. matthew.powner@ucl.ac.uk.
authors.forename: M W
authors.identifier: http://orcid.org/0000-0002-6368-3190
authors.initials: MW
authors.lastname: Powner
mesh_terms: D000171:Acrolein / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D019418:Evolution, Chemical; D015394:Molecular Structure; D000069497:Origin of Life; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010085:Oxidative Phosphorylation; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D004852:Epoxy Compounds; D010080:Oxazoles; D014867:Water; D000171:Acrolein; C007871:glycinaldehyde