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Mixed Anhydride Intermediates in the Reaction of 5(4 H)-Oxazolones with Phosphate Esters and Nucleotides.
- Source :
-
Chemistry - A European Journal . 10/10/2016, Vol. 22 Issue 42, p14940-14949. 10p. - Publication Year :
- 2016
-
Abstract
- 5(4 H)-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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ANHYDRIDES
*NUCLEOTIDES
*PEPTIDES
*PHOSPHATES
*PREBIOTICS
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 22
- Issue :
- 42
- Database :
- Academic Search Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 118514333
- Full Text :
- https://doi.org/10.1002/chem.201602697