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- Title
Ester-Mediated Amide Bond Formation Driven by Wet-Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth.
- Authors
Forsythe, Jay G.; Yu, Sheng ‐ Sheng; Mamajanov, Irena; Grover, Martha A.; Krishnamurthy, Ramanarayanan; Fernández, Facundo M.; Hud, Nicholas V.
- 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.
- Subjects
BOND formation mechanism; CHEMICAL bonds; AMIDES; POLYPEPTIDES; DEPSIPEPTIDES
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 34, p10009
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201503792