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

Jay G. Forsythe, Sheng Sheng Yu, Irena Mamajanov, Martha A. Grover, Ramanarayanan Krishnamurthy, Facundo M. Fernández, Nicholas V. Hud

Research output: Contribution to journalArticlepeer-review

133 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9871-9875
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number34
DOIs
Publication statusPublished - 2015 Aug 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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