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.