Ester‐Mediated Amide Bond Formation Driven by Wet–Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth |
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Authors: | Dr. Jay G. Forsythe Sheng‐Sheng Yu Dr. Irena Mamajanov Prof. Martha A. Grover Prof. Ramanarayanan Krishnamurthy Prof. Facundo M. Fernández Prof. Nicholas V. Hud |
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Affiliation: | 1. NSF/NASA Center for Chemical Evolution (USA);2. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA (USA);3. School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA (USA);4. Department of Chemistry, The Scripps Research Institute, La Jolla, CA (USA) |
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Abstract: | Although it is generally accepted that amino acids were present on the prebiotic Earth, the mechanism by which α‐amino acids were condensed into polypeptides before the emergence of enzymes remains unsolved. Here, we demonstrate a prebiotically plausible mechanism for peptide (amide) bond formation that is enabled by α‐hydroxy acids, which were likely present along with amino acids on the early Earth. Together, α‐hydroxy acids and α‐amino acids form depsipeptides—oligomers with a combination of ester and amide linkages—in model prebiotic reactions that are driven by wet–cool/dry–hot cycles. Through a combination of ester–amide bond exchange and ester bond hydrolysis, depsipeptides are enriched with amino acids over time. These results support a long‐standing hypothesis that peptides might have arisen from ester‐based precursors. |
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Keywords: | chemical evolution day– night cycle depsipeptides origins‐of‐life proto‐peptides |
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