Lipase-supported synthesis of peptidic hydrogels

Abstract

Self-assembling gelling peptides are increasingly being investigated as defined biomatrices for biomedical applications. Using an enzymatic reaction to convert a precursor into a hydrogelator one can control or modulate functions and responses of a hydrogel, depending on its preparation conditions. This work details the self-assembly, under physiological conditions, of amphiphilic building blocks consisting of tripeptides (Phe₃) linked to fluorenylmethoxycarbonyl (Fmoc) obtained by using a lipase to link an Fmoc–Phe amino acid to the dipeptide diphenylalanine (Phe₂). The viscoelastic properties of the tripeptides obtained were investigated. SEM and AFM images of Fmoc–peptides confirmed that they self-assemble to generate supramolecular aggregates driven by π–π stacking interactions of the Fmoc groups.