caa a22 4500 465744680 CHVBK 20180323111817.0 cr unu---uuuuu 170327e19900501xx s 000 0 eng 10.1007/BF01808107 doi (NATIONALLICENCE)springer-10.1007/BF01808107 Diketopiperazine-mediated peptide formation in aqueous solution [Elektronische Daten] [M. Nagayama, O. Takaoka, K. Inomata, Y. Yamagata] Though diketopiperazines (DKP) are formed in most experiments concerning the prebiotic peptide formation, the molecules have not been paid attention in the studies of chemical evolution. We have found that triglycine, tetraglycine or pentaglycine are formed in aqueous solution of glycine anhydride (DKP) and glycine, diglycine or triglycine, respectively. A reaction of alanine with DKP resulted in the formation of glycylglycylalanine under the same conditions. These results indicate that the formation of the peptide bonds proceeds through the nucleophilic attack of an amino group of the amino acids or the oligoglycines on the DKP accompanied by the ring-opening. The formation of glycine anhydride, di-, tri- and tetraglycine was also observed in a mixed aqueous solution of urea and glycine in an open system to allow the evaporation of ammonia. A probable pathway is proposed for prebiotic peptide formation through diketopiperazine on the primitive Earth. Kluwer Academic Publishers, 1990 Nagayama M. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut Takaoka O. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut Inomata K. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut Yamagata Y. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut Origins of life and evolution of the biosphere Kluwer Academic Publishers 20/3-4(1990-05-01), 249-257 0169-6149 20:3-4<249 1990 20 11084 https://doi.org/10.1007/BF01808107 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF01808107 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Nagayama M. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut NATIONALLICENCE 700 1- Takaoka O. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut NATIONALLICENCE 700 1- Inomata K. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut NATIONALLICENCE 700 1- Yamagata Y. Department of Physics and Department of Chemistry, Faculty of Science, Kanzawa University, Marunouchi 1-1, 920, Kanazawa, Japan aut NATIONALLICENCE 773 0- Origins of life and evolution of the biosphere Kluwer Academic Publishers 20/3-4(1990-05-01), 249-257 0169-6149 20:3-4<249 1990 20 11084 Metadata rights reserved Springer special CC-BY-NC licence nationallicence SWISSBIB 465122213 BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer