Dataset Information

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

ABSTRACT: Although it is generally accepted that amino acids were present on the prebiotic Earth, the mechanism by which ?-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 ?-hydroxy acids, which were likely present along with amino acids on the early Earth. Together, ?-hydroxy acids and ?-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.

SUBMITTER: Forsythe JG

PROVIDER: S-EPMC4678426 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Publications

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

Forsythe Jay G JG Yu Sheng-Sheng SS Mamajanov Irena I Grover Martha A MA Krishnamurthy Ramanarayanan R Fernández Facundo M FM Hud Nicholas V NV

Angewandte Chemie (International ed. in English) 20150715 34

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 ...[more]

PMID: 26201989

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Dataset Information

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

Publications

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

Similar Datasets

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