title: The Prebiotic C-Terminal Elongation of Peptides Can Be Initiated by N-Carbamoyl Amino Acids.
abstract: The formation of peptides upon 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)-promoted activation of N-carbamoylamino acids (CAA), was considered in the scope of our recent works on carbodiimide promoted C-terminus elongation of peptides in a prebiotic context. Thus EDC promoted activation of CAA derivatives of Tyr(Me) or Ala in dilute aqueous medium pH 5.5-6.5 in the presence of excess of AA, resulted in peptide formation by C-terminus activation/elongation. Kinetic results similar to those of EDC-mediated activation of N-acyl-AA lead us to postulate the formation of a 2-amino-5(4H)-oxazolone intermediate by cyclization of the activated CAA, in spite of the absence of epimerization occurred at CAA residues. Thus, in a prebiotic context, CAA may have played a similar role as N-acyl-AA in the initiation of C-terminus peptide elongation.
authors.affiliation: Physique des Interactions Ioniques et Moléculaires, UMR 7345, Aix-Marseille Université, CNRS, Centre St-Jérôme, Case 252, Avenue Escadrille Normandie-Niemen, 13397, Marseille, France.
authors.forename: Ninette
authors.initials: N
authors.lastname: Abou Mrad
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, University of Montpellier, ENSCM, Place Bataillon, 34095, Montpellier cedex 5, France.
authors.forename: Ghinwa
authors.initials: G
authors.lastname: Ajram
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, University of Montpellier, ENSCM, Place Bataillon, 34095, Montpellier cedex 5, France.
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Rossi
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, University of Montpellier, ENSCM, Place Bataillon, 34095, Montpellier cedex 5, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Boiteau
authors.affiliation: Physique des Interactions Ioniques et Moléculaires, UMR 7345, Aix-Marseille Université, CNRS, Centre St-Jérôme, Case 252, Avenue Escadrille Normandie-Niemen, 13397, Marseille, France.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Duvernay
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, University of Montpellier, ENSCM, Place Bataillon, 34095, Montpellier cedex 5, France.
authors.forename: Robert
authors.initials: R
authors.lastname: Pascal
authors.affiliation: Physique des Interactions Ioniques et Moléculaires, UMR 7345, Aix-Marseille Université, CNRS, Centre St-Jérôme, Case 252, Avenue Escadrille Normandie-Niemen, 13397, Marseille, France.
authors.forename: Grégoire
authors.initials: G
authors.lastname: Danger
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism*; D010452:Peptide Biosynthesis / Q000502:physiology*; D010455:Peptides / Q000737:chemistry / Q000378:metabolism*; D056692:Prebiotics
chemical_list: D000596:Amino Acids; D010455:Peptides; D056692:Prebiotics; C050632:polypeptide C
keywords: C-terminus activation; amino acids; oxazolones; peptides; reactive intermediates