We found a match
Your institution may have rights to this item. Sign in to continue.
- 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; AMIDES; POLYPEPTIDES; OLIGOMERS; CHEMICAL reactions
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 34, p9871
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201503792