Angew. Chem. Int. Ed.:Abiotic Formation of an Amide Bond via Surface-Supported Direct Carboxyl-Amine Coupling

Date:2021-12-22Keywords:迟力峰教授课题组View:841

Amide bond formation is one of the most important reactions in biochemistry, notably being of crucial importance for the origin of life. Herein, we combine scanning tunneling microscopy and X-ray photoelectron spectroscopy studies to provide evidence for thermally activated abiotic formation of amide bonds between  adsorbed precursors through direct carboxyl-amine coupling under ultrahigh vacuum conditions by means of on-surface synthesis. Complementary insights from temperature- programmed desorption measurements and density functional theory calculations reveal the competition between cross-coupling amide formation and decarboxylation reactions on the Au(111) surface. Furthermore, we demonstrate the critical influence of the employed metal support: whereas on Au(111) the coupling readily occurs, different reaction scenarios prevail on Ag(111) and Cu(111). The systematic experiments signal that archetypical bio-related molecules can be abiotically synthesized in clean environments without water or oxygen.

Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202113590