Differently N‐Capped Analogues of Fmoc‐FF

Abstract

Short and ultra-short peptides have been recently envisioned as excellent building blocks for the formulation of hydrogels with appealing properties. Due to its simplicity and capability to gel under physiological conditions, Fmoc-FF (N αfluorenylmethoxycarbonyl-diphenylalanine), remains one of the most studied low molecular-weight hydrogelators. Since its first identification in 2006, a plethora of its analogues were synthetized and investigated for the fabrication of novel supramolecular materials. Here we report a description of the Fmoc-FF analogues in which the aromatic Fmoc group is replaced with other substituents. These analogues are distinguished into five different classes including derivatives: i) customized with solid phase peptide synthesis protecting groups; ii) containing non-aromatic groups, iii) containing aromatic groups, iv) derivatized with metal complexes and v) containing stimuli-responsive groups. The morphological, mechanical, and functional effects caused by this modification on the resulting material are also pointed out.

Investigating the complexation propensity of self-assembling dipeptides with the anticancer peptide-drug Bortezomib: a computational study

“…Moreover, the Fmoc-FF and Z-FF hydrogel forming propensity has been previously established using thorough theoretical and experimental studies. 68–71…”

A Light Scattering Investigation of Enzymatic Gelation in Self-Assembling Peptides

“…The methodology we used in this work, can be extended to other base-triggered molecular gelators [ 19 , 20 ]. Understanding the possible effect of the urea–urease reaction in the self-assembly of urea-based SAPs [ 25 ], is particularly tempting.…”

“…In recent years, self-assembling peptides (SAPs) have been commonly used as gelators, because they form nanofibrous matrices that resemble the fibrillar matrix of the natural ECM [ 16 ]. In order to trigger the self-assembly, an external stimulus is usually needed [ 4 , 17 ], such as adding a co-solvent [ 18 , 19 , 20 , 21 ], irradiating the sample with UV light [ 22 , 23 ], varying the temperature [ 24 , 25 ], or changing the ionic strength [ 26 ] or the pH of the system [ 27 , 28 , 29 , 30 , 31 ].…”

RAFT-synthesis and self-assembly-induced emission of pendant diphenylalanine–tetraphenylethylene copolymers

“…Thus, the diphenylalanine motif can be employed in a wide range of potential applications involving bioinspired nanomaterials (e.g., antimicrobial activity 30,31 and biosensors 32,33 ), devices (e.g., piezoelectrics 34,35 ), and material design (e.g., templates 24 and gels 36,37 ). There are also intriguing examples of the application of the properties of AIE moiety-containing diphenylalanine derivatives, 38,39 such as the formation of microtubes, 40,41 gels, 42,43 peptidyl nanostructures, 44 and nanoparticles. 45 In addition, AIE probes have been used to investigate the mechanistic aspects of anti-amyloid compounds by interaction with diphenylalanine.…”

“…, templates 24 and gels 36,37 ). There are also intriguing examples of the application of the properties of AIE moiety-containing diphenylalanine derivatives, 38,39 such as the formation of microtubes, 40,41 gels, 42,43 peptidyl nanostructures, 44 and nanoparticles. 45 In addition, AIE probes have been used to investigate the mechanistic aspects of anti-amyloid compounds by interaction with diphenylalanine.…”