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Oxidative peptide (and amide) formation from Schiff base complexes

B L Strehler, P Schmid, M P Li

    Journal of Molecular Evolution
    |January 1, 1982
    PubMed
    Summary
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    This study demonstrates a potential pathway for the origin of life, showing that specific polypeptides can template complementary poly-Schiff bases. These can then be oxidized to form peptide linkages, yielding original peptide polymers.

    Area of Science:

    • * Origin of Life research
    • * Biochemistry and prebiotic chemistry

    Background:

    • * Hypothesizes that early replicating molecules were specific polypeptides.
    • * Proposes a template mechanism involving poly-Schiff bases and oxidation to peptide linkages.
    • * Suggests a double cycle of complementary replication could form original peptide polymers.

    Purpose of the Study:

    • * To investigate the feasibility of a proposed prebiotic peptide synthesis model.
    • * To test if Schiff base formation followed by oxidation can yield dipeptides from amino aldehydes and amino acids.

    Main Methods:

    • * Formation of a Schiff-base complex between N-acetyl-tyrosinal and tyrosine in aqueous solution at pH 9.
    • * Oxidation of the Schiff-base complex using hydrogen peroxide (H2O2).

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  • * Analysis of reaction products to identify formed peptides and amino acids.

    • Main Results:

    • * High yield production of the substituted dipeptide, N-acetyl-tyrosyl-tyrosine.
    • * Demonstrated formation of a variety of N-acyl amino acids from amino acids and aliphatic aldehydes under similar conditions.
    • * Successful synthesis of dipeptides via Schiff base complex oxidation in aqueous solution.

    Conclusions:

    • * The study supports the hypothesis that specific polypeptides could have served as templates for early life's replicating molecules.
    • * Prebiotic synthesis of peptides via Schiff base intermediates and oxidation is chemically plausible.
    • * The findings provide experimental evidence for a potential pathway in the origin of peptide-based biological systems.