Self-Assembly Propensity Dictates Lifetimes in Transient Naphthalimide–Dipeptide Nanofibers

Mohit Kumar, Deborah Sementa, Vishal Narang, Elisa Riedo, Rein V. Ulijn

Research output: Contribution to journalArticle

Abstract

Transient self-assembly of dipeptide nanofibers with lifetimes that are predictably variable through dipeptide sequence design are presented. This was achieved using 1,8-naphthalimide (NI) amino acid methyl-esters (Phe, Tyr, Leu) that are biocatalytically coupled to amino acid-amides (Phe, Tyr, Leu, Val, Ala, Ser) to form self-assembling NI-dipeptides. However, competing hydrolysis of the dipeptides results in disassembly. It was demonstrated that the kinetic parameters like lifetimes of these nanofibers can be predictably regulated by the thermodynamic parameter, namely the self-assembly propensity of the constituent dipeptide sequence. These lifetimes could vary from minutes, to hours, to permanent gels that do not degrade. Moreover, the in-built NI fluorophore was utilized to image the transient nanostructures in solution with stimulated emission depletion (STED) based super-resolution fluorescence microscopy.

Original languageEnglish (US)
Pages (from-to)8372-8376
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number38
DOIs
StatePublished - Jul 8 2020

Keywords

  • biocatalysis
  • peptide nanotechnology
  • self-assembly
  • systems chemistry
  • transient nanostructure

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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