Mixed Anhydride Intermediates in the Reaction of 5(4 H )-Oxazolones with Phosphate Esters and Nucleotides - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2016

Mixed Anhydride Intermediates in the Reaction of 5(4 H )-Oxazolones with Phosphate Esters and Nucleotides

Résumé

Abstract 5(4H)‐Oxazolones can be formed through the activation of acylated α‐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 α‐amino acids and nucleotides.

Domaines

Chimie
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Origine : Publication financée par une institution

Dates et versions

hal-03541262 , version 1 (24-01-2022)

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Paternité - Pas d'utilisation commerciale

Identifiants

Citer

Ziwei Liu, Lukas Rigger, Jean-Christophe Rossi, John Sutherland, Robert Pascal. Mixed Anhydride Intermediates in the Reaction of 5(4 H )-Oxazolones with Phosphate Esters and Nucleotides. Chemistry - A European Journal, 2016, 22 (42), pp.14940-14949. ⟨10.1002/chem.201602697⟩. ⟨hal-03541262⟩
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