N-carbamoyl amino acid solid-gas nitrosation by NO/NOx: A new route to oligopeptides via alpha-amino acid N-carboxyanhydride. Prebiotic implications.
Alpha-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 NOx. 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).
Taillades
J
J
Organisation Moléculaire-Evolution et Matériaux Fluorés, Chemistry Department, University of Montpellier II, CC 017, Place E. Bataillon, 34095 Montpellier Cedex 5, France.
Collet
H
H
Garrel
L
L
Beuzelin
I
I
Boiteau
L
L
Choukroun
H
H
Commeyras
A
A
D000596:Amino Acids / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009569:Nitric Oxide / Q000737:chemistry; D015538:Nitrosation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010452:Peptide Biosynthesis; D014633:Valine / Q000737:chemistry
D000596:Amino Acids; D009842:Oligopeptides; D009569:Nitric Oxide; D014633:Valine; D010100:Oxygen; D005998:Glycine