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

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,...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-07, Vol.26 (38), p.8372-8376
Main Authors: Kumar, Mohit, Sementa, Deborah, Narang, Vishal, Riedo, Elisa, Ulijn, Rein V.
Format: Article
Language:English
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Summary: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. Time‐programmable, transient supramolecular naphthalimide‐dipeptide nanofibers were reported, the lifetimes of which are predictably variable, demonstrated through variation of the self‐assembly propensity of their amino acid precursors. Thus, the work shows that a thermodynamic parameter dictates kinetic lifetimes in transient fibers formed by competing biocatalytic self‐assembly and disassembly of aromatic peptide amphiphiles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202001008