Ester-Mediated Amide Bond Formation Driven by Wet-Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-08, Vol.54 (34), p.9871-9875
Main Authors: Forsythe, Jay G., Yu, Sheng-Sheng, Mamajanov, Irena, Grover, Martha A., Krishnamurthy, Ramanarayanan, Fernández, Facundo M., Hud, Nicholas V.
Format: Article
Language:English
Subjects:
Amides
Amides - chemistry
Amino acids
Bonding
chemical evolution
Communications
day-night cycle
depsipeptides
Earth
Earth, Planet
Esters
Esters - chemistry
Evolution, Chemical
Hydroxy acids
Oligomers
Origin of Life
origins-of-life
Peptides
Peptides - chemical synthesis
Peptides - chemistry
Polypeptides
Prebiotics
proto-peptides
Temperature
Water - chemistry
Wettability
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Summary: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. Amino acids form peptide bonds when subjected to day–night cycles (wet–dry cycles) in the presence of hydroxy acids. Such a reaction could have occurred on the prebiotic Earth.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201503792