Emergent Catalytic Behavior of Self‐Assembled Low Molecular Weight Peptide‐Based Aggregates and Hydrogels

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  • Marta Tena‐Solsona
    Departament de Química Inorgànica i Orgànica Universitat Jaume I 12071 Castelló Spain
  • Jayanta Nanda
    Department of Chemistry Ben-Gurion University of the Negev Be'er Sheva Israel
  • Santiago Díaz‐Oltra
    Departament de Química Inorgànica i Orgànica Universitat Jaume I 12071 Castelló Spain
  • Agata Chotera
    Department of Chemistry Ben-Gurion University of the Negev Be'er Sheva Israel
  • Gonen Ashkenasy
    Department of Chemistry Ben-Gurion University of the Negev Be'er Sheva Israel
  • Beatriu Escuder
    Departament de Química Inorgànica i Orgànica Universitat Jaume I 12071 Castelló Spain

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<jats:title>Abstract</jats:title><jats:p>We report a series of short peptides possessing the sequence (FE)<jats:sub><jats:italic>n</jats:italic></jats:sub> or (EF)<jats:sub><jats:italic>n</jats:italic></jats:sub> and bearing <jats:sc>l</jats:sc>‐proline at their N‐terminus that self‐assemble into high aspect ratio aggregates and hydrogels. We show that these aggregates are able to catalyze the aldol reaction, whereas non‐aggregated analogues are catalytically inactive. We have undertaken an analysis of the results, considering the accessibility of catalytic sites, p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> value shifts, and the presence of hydrophobic pockets. We conclude that the presence of hydrophobic regions is indeed relevant for substrate solubilization, but that the active site accessibility is the key factor for the observed differences in reaction rates. The results presented here provide an example of the emergence of a new chemical property caused by self‐assembly, and support the relevant role played by self‐assembled peptides in prebiotic scenarios. In this sense, the reported systems can be seen as primitive aldolase I mimics, and have been successfully tested for the synthesis of simple carbohydrate precursors.</jats:p>

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