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

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TitleEster-Mediated Amide Bond Formation Driven by Wet-Dry Cycles: A Possible Path to Polypeptides on the Prebiotic Earth.
Publication TypeJournal Article
Year of Publication2015
AuthorsForsythe, JG, Yu, S-S, Mamajanov, I, Grover, MA, Krishnamurthy, R, Fernández, FM, Hud, NV
JournalAngew Chem Int Ed Engl
Volume54
Issue34
Pagination9871-5
Date Published2015 Aug 17
ISSN1521-3773
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.
DOI10.1002/anie.201503792
Alternate JournalAngew. Chem. Int. Ed. Engl.
PubMed ID26201989