A Possible Path To Prebiotic Peptides Involving Silica And Hydroxy Acid-Mediated Amide Bond Formation

Keywords

amino acids; chemical evolution; depsipeptides; silicates; surface chemistry

Abstract

The formation of alanine and glycine oligomers in films produced by drying aqueous mixtures of lactic acid and silica nanoparticles has been studied as a model prebiotic reaction. The addition of silica results in alanine or glycine enrichment in the polymers. Oligomerization proceeds through ester-mediated peptide bond formation in an acidic and evaporative environment at temperatures as low as 85 °C. For both amino acids, the dominant species produced in the presence of silica and lactic acid are rich in amide bonds and deficient in ester linkages. At higher temperatures, glycine and alanine oligomers contain only a single hydroxy acid residue conjugated to the peptide N terminus. Similar product distributions occur with silica particles prereacted with lactic acid, which suggests the catalytic role of a functionalized surface. This work highlights the role minerals might have served in transitioning from oligomers with both ester and amide linkages (depsipeptides) to peptides in a prebiotic context.

Publication Date

9-17-2018

Publication Title

ChemBioChem

Volume

19

Issue

18

Number of Pages

1913-1917

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1002/cbic.201800217

Socpus ID

85053064143 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/85053064143

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