Danger Grégoire, Boiteau Laurent, Cottet Hervé, Pascal Robert
Dynamique des Systèmes Biomoléculaires Complexes, UMR 5073, Université Montpellier 2, CNRS, CC 017, 34095 Montpellier Cedex 5, France.
J Am Chem Soc. 2006 Jun 14;128(23):7412-3. doi: 10.1021/ja061339+.
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.
与许多尿素类似，N-氨基甲酰氨基酸在接近中性pH的水溶液中通过消除机制水解，水的亲核攻击是一个次要过程。可以发生两种相互竞争的消除机制，涉及氰酸酯或异氰酸酯瞬态中间体。观察到肽的形成，并将其归因于通过氨基酸N-羧基酐（NCA）中间体的后一种途径。最终，氰酸酯及其前体（包括尿素）由于其使氨基酸氨甲酰化的能力，意外地表现为氨基酸活化剂。由于其在原始地球上产生NCA的背景益生元生产的能力，该反应被认为对生命起源过程有贡献。
