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

Marta Tena-Solsona, Jayanta Nanda, Santiago Díaz-Oltra, Agata Chotera, Gonen Ashkenasy, Beatriu Escuder

Research output: Contribution to journalArticlepeer-review

102 Scopus citations


We report a series of short peptides possessing the sequence (FE)n or (EF)n and bearing l-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, pKa 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.

Original languageEnglish
Pages (from-to)6687-6694
Number of pages8
JournalChemistry - A European Journal
Issue number19
StatePublished - 4 May 2016


  • aldol reaction
  • gels
  • peptides
  • self-assembly
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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