Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides |
| |
| Authors: | Dr Ziwei Liu Dr Lukas Rigger Dr Jean‐Christophe Rossi Prof?Dr John D Sutherland Dr Robert Pascal |
| |
| Affiliation: | 1. Institut des Biomolécules Max Mousseron, CNRS, Université de Montpellier, école nationale supérieure de chimie de Montpellier (ENSCM), Montpellier Cedex 5, France;2. MRC Laboratory of Molecular Biology, Cambridge, UK |
| |
| 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. |
| |
| Keywords: | anhydrides nucleotides peptides phosphates prebiotic chemistry |
|
|
