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Journal of Molecular Evolution

, Volume 48, Issue 6, pp 638–645 | Cite as

N-Carbamoyl Amino Acid Solid–Gas Nitrosation by NO/NO x : A New Route to Oligopeptides via α-Amino Acid N-Carboxyanhydride. Prebiotic Implications

  • Jacques  Taillades
  • Hélène  Collet
  • Laurence  Garrel
  • Isabelle  Beuzelin
  • Laurent  Boiteau
  • Henri  Choukroun
  • Auguste  Commeyras

Abstract.

α-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NO x . Nitrosation of solid CAA (glycine or valine derivative) by a 4/1 NO/O2 gaseous mixture (1 atm) yields N-carboxyanhydride (NCA) quantitatively in less than 1 h at room temperature. The crude solid NCA undergoes quantitative oligomerization (from trimer to nonamer under the conditions we used) when treated with a (bi)carbonate aqueous buffer at pH 9. We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase (``drying-lagoon'' scenario).

Key words: Prebiotic — Peptides — Nitrosation — Nitric oxide —N-Carbamoyl amino acid —N-Carboxyanhydride — Drying lagoon 

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Copyright information

© Springer-Verlag New York Inc. 1999

Authors and Affiliations

  • Jacques  Taillades
    • 1
  • Hélène  Collet
    • 1
  • Laurence  Garrel
    • 1
  • Isabelle  Beuzelin
    • 1
  • Laurent  Boiteau
    • 1
  • Henri  Choukroun
    • 1
  • Auguste  Commeyras
    • 1
  1. 1.Organisation Moléculaire—Evolution et Matériaux Fluorés, Chemistry Department, University of Montpellier II, CC 017, Place E. Bataillon, 34095 Montpellier Cedex 5, FranceFR

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