Kinetics of prebiotic depsipeptide formation from the ester–amide exchange reaction

作者: F. Joseph Schork , Martha A. Grover , Sheng-Sheng Yu , Ramanarayanan Krishnamurthy , Facundo M. Fernández

DOI: 10.1039/C6CP05527C

关键词:

摘要: In this work, we introduce a kinetic model to study the effectiveness of ester-mediated amide bond formation under prebiotic conditions. our previous found that simple system composed α-hydroxy acids and α-amino is capable forming peptide bonds via esterification followed by ester–amide exchange reaction. To further understand behavior copolymerization, first tracked growth initial species from valine/lactic acid mixture in closed reactor. A mathematical was developed simulate reactions evaluate rate constants at different temperatures. We these can be described empirical Arrhenius equation even when reaction occurred solid (dry) state. Further calculations for activation parameters showed pathway facilitates lowering entropies. These results provide theoretical framework illustrates why efficient it would have been more favorable on early Earth, compared without aid hydroxy acids.

参考文章(33)
Uma Shanker, Brij Bhushan, G. Bhattacharjee, Kamaluddin, Oligomerization of Glycine and Alanine Catalyzed by Iron Oxides: Implications for Prebiotic Chemistry Origins of Life and Evolution of Biospheres. ,vol. 42, pp. 31- 45 ,(2012) , 10.1007/S11084-012-9266-5
W. F. K. Wynne‐Jones, Henry Eyring, The Absolute Rate of Reactions in Condensed Phases The Journal of Chemical Physics. ,vol. 3, pp. 492- 502 ,(1935) , 10.1063/1.1749713
S. L. Miller, H. C. Urey, Organic Compound Synthesis on the Primitive Earth Science. ,vol. 130, pp. 245- 251 ,(1959) , 10.1126/SCIENCE.130.3370.245
Mark T. Hamann, Paul J. Scheuer, Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp Journal of the American Chemical Society. ,vol. 115, pp. 5825- 5826 ,(1993) , 10.1021/JA00066A061
Everett L Shock, Stability of peptides in high-temperature aqueous solutions Geochimica et Cosmochimica Acta. ,vol. 56, pp. 3481- 3491 ,(1992) , 10.1016/0016-7037(92)90392-V
Bernd Michael Rode, Peptides and the origin of life1 Peptides. ,vol. 20, pp. 773- 786 ,(1999) , 10.1016/S0196-9781(99)00062-5
Jay G. Forsythe, Sheng-Sheng Yu, Irena Mamajanov, Martha A. Grover, Ramanarayanan Krishnamurthy, Facundo M. Fernández, Nicholas V. Hud, Ester‐Mediated Amide Bond Formation Driven by Wet–Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth Angewandte Chemie. ,vol. 54, pp. 9871- 9875 ,(2015) , 10.1002/ANIE.201503792
Grégoire Danger, Raphaël Plasson, Robert Pascal, Pathways for the formation and evolution of peptides in prebiotic environments Chemical Society Reviews. ,vol. 41, pp. 5416- 5429 ,(2012) , 10.1039/C2CS35064E
Tatsuro Ouchi, Tatsuya Nozaki, Akira Ishikawa, Isao Fujimoto, Yuichi Ohya, Synthesis and enzymatic hydrolysis of lactic acid–depsipeptide copolymers with functionalized pendant groups Journal of Polymer Science Part A. ,vol. 35, pp. 377- 383 ,(1997) , 10.1002/(SICI)1099-0518(19970130)35:2<377::AID-POLA21>3.0.CO;2-L
S. Trobro, J. Aqvist, Mechanism of peptide bond synthesis on the ribosome. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 102, pp. 12395- 12400 ,(2005) , 10.1073/PNAS.0504043102