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7177457 
Journal Article 
The Prebiotic C-Terminal Elongation of Peptides Can Be Initiated by N-Carbamoyl Amino Acids 
Abou Mrad, N; Ajram, G; Rossi, JC; Boiteau, L; Duvernay, F; Pascal, R; Danger, G; , 
2017 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
23 
31 
7418-7421 
English 
28378889 
WOS:000402648500005 
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.