Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 42, Pages 14940-14949Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602697
Keywords
anhydrides; nucleotides; peptides; phosphates; prebiotic chemistry
Categories
Funding
- Simons Foundation [293065]
- Agence Nationale de la Recherche [ANR-14-CE33-0020-01]
- COST action [CM1304]
- Medical Research Council [MC_UP_A024_1009] Funding Source: researchfish
- MRC [MC_UP_A024_1009] Funding Source: UKRI
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5(4H)-Oxazolones can be formed through the activation of acylated alpha-amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic-phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono-substituted phosphate group at the 3'- or 5'-terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3'-terminus are considered to be particularly relevant to the common prebiotic chemistry of alpha-amino acids and nucleotides.
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