Elongation of Model Prebiotic Proto-Peptides by Continuous Monomer Feeding

Sheng Sheng Yu, Martin D. Solano, Matthew K. Blanchard, Molly T. Soper-Hopper, Ramanarayanan Krishnamurthy, Facundo M. Fernández, Nicholas V. Hud, F. Joseph Schork, Martha A. Grover

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Mixtures of amino acids with hydroxy acids allow for the formation of peptide bonds in a plausible prebiotic scenario via ester bond formation followed by ester-amide exchange. Here, we investigate the ability of the ester-mediated reaction pathway to form even longer polymers with peptide backbones based on the specific details of the reaction protocol. Fresh monomers were fed to the polymer/monomer mixture periodically by an automated "day-night machine" that was designed to simulate wet-dry cycles that would have been common on the prebiotic Earth. Quantitative analysis of peptide bond formation in the complex oligomer mixture was enabled by a simple hydrolysis treatment. In the ester-mediated peptide elongation process, new monomers add to one end of the chain step-by-step without termination. The feed composition (hydroxy acids and/or amino acids) was found to determine the final oligomer distribution. Production of longer oligomers enriched in peptide bonds was more efficient when only amino acids were fed because of a smaller number of active oligomer chains. These results reveal a process for synthesizing longer depsipeptides and/or peptides that could form secondary structures, and possibly functional polymers.

Original languageEnglish
Pages (from-to)9286-9294
Number of pages9
JournalMacromolecules
Volume50
Issue number23
DOIs
Publication statusPublished - 2017 Dec 12

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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