The effect of l-DOPA hydroxyl groups on the formation of supramolecular hydrogels

Abstract

Fmoc-L-DOPA-D-Oxd-OH was prepared starting from commercially available L-DOPA. Its gelation ability was tested by comparison with Fmoc-L-Tyr-D-Oxd-OH and Fmoc-L-Phe-D-Oxd-OH using ten different triggers. Among them, only GdL, CaCl₂ and ZnCl₂ form strong hydrogels with the three gelators. The analysis of the aerogels obtained by freeze drying the hydrogels show that the three gelators always induce the formation of dense networks, which strongly depend on the nature of the gelator. Rheological analysis of these samples demonstrates that stronger gels were obtained using the L-Tyr containing gelator, while the L-DOPA containing hydrogels were characterized by a storage modulus approximately one order of magnitude lower. Finally, the L-Phe containing gelators show a different trend with respect to the other samples depending on the trigger used. All the hydrogels show a thixotropic behaviour at the molecular level. These results indicate that hydrogel formation is sensitive to both the number of the hydroxyl moieties on the aromatic rings and trigger used.