The Prebiotic C-Terminal Elongation of Peptides Can Be Initiated by N-Carbamoyl Amino Acids
| Autor: | Grégoire Danger, Fabrice Duvernay, Jean-Christophe Rossi, Ghinwa Ajram, Laurent Boiteau, Robert Pascal, Ninette Abou Mrad |
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| Přispěvatelé: | Aix Marseille Université (AMU), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Physique des interactions ioniques et moléculaires (PIIM), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2017 |
| Předmět: |
Peptide Biosynthesis
Stereochemistry medicine.medical_treatment Context (language use) Peptide 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound mental disorders medicine Amino Acids ComputingMilieux_MISCELLANEOUS Carbodiimide chemistry.chemical_classification 010405 organic chemistry Peptide formation [CHIM.ORGA]Chemical Sciences/Organic chemistry Prebiotic Organic Chemistry nutritional and metabolic diseases General Chemistry 0104 chemical sciences Amino acid Prebiotics chemistry Epimer Elongation [CHIM.OTHE]Chemical Sciences/Other Peptides |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2017, 23 (31), pp.7418-7421. ⟨10.1002/chem.201700702⟩ Chemistry-A European Journal, 2017, 23 (31), pp.7418-7421. ⟨10.1002/chem.201700702⟩ |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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