The Peptide Formation Mediated by Cyanate Revisited. N-Carboxyanhydrides as Accessible Intermediates in the Decomposition of N-Carbamoylaminoacids - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2006

The Peptide Formation Mediated by Cyanate Revisited. N-Carboxyanhydrides as Accessible Intermediates in the Decomposition of N-Carbamoylaminoacids

Résumé

Similar to many ureas, N-carbamoylamino acids were shown to be hydrolyzed in aqueous solution through elimination mechanisms at close to neutral pH, the nucleophilic attack of water being a minor process. Two competing elimination mechanisms can take place involving either cyanate or isocyanate transient intermediates. Peptide formation was observed and attributed to the latter pathway through the intermediacy of amino acid N-carboxyanhydride (NCA). Eventually, cyanate and its precursors (including urea) unexpectedly behave as amino acid activating agents because of their ability in amino acid carbamoylation. Owing to its ability to generate a background prebiotic production of NCAs on the primitive Earth, this reaction is suggested to have contributed to the origin of life process.

Domaines

Chimie organique

Dates et versions

hal-00134565 , version 1 (02-03-2007)

Identifiants

Citer

Robert Pascal, Grégoire Danger, Laurent Boiteau, Hervé Cottet. The Peptide Formation Mediated by Cyanate Revisited. N-Carboxyanhydrides as Accessible Intermediates in the Decomposition of N-Carbamoylaminoacids. Journal of the American Chemical Society, 2006, 128, pp.7412-7413. ⟨10.1021/ja061339+⟩. ⟨hal-00134565⟩
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