Aromatic peptide amphiphiles: significance of the Fmoc moiety

Fmoc-2-mercaptobenzothiazole, for the introduction of the Fmoc moiety free of side-reactions.

A double side-reaction, consisting in the formation of Fmoc-beta-Ala-OH and Fmoc-beta-Ala-AA-OH, during the preparation of Fmoc protected amino acids (Fmoc-AA-OH) with Fmoc-OSu is discussed. Furthermore, the new Fmoc-2-MBT reagent is proposed for avoiding these side-reactions as well as the formation of the Fmoc-dipeptides (Fmoc-AA-AA-OH) and even tripeptides, which is another important side-re...

Peptide based amphiphiles.

Extracellular matrix formation in self-assembled minimalistic bioactive hydrogels based on aromatic peptide amphiphiles

The hitherto inconsistency in clinical performance for engineered skin drives the current development of novel cell-scaffolding materials; one challenge is to only extract essential characteristics from the complex native ECM (extracellular matrix) and incorporate them into a scaffold with minimal complexity to support normal cell functions. This study involved small-molecule-based bioactive hy...

Advances in Fmoc solid‐phase peptide synthesis

Today, Fmoc SPPS is the method of choice for peptide synthesis. Very-high-quality Fmoc building blocks are available at low cost because of the economies of scale arising from current multiton production of therapeutic peptides by Fmoc SPPS. Many modified derivatives are commercially available as Fmoc building blocks, making synthetic access to a broad range of peptide derivatives straightforwa...

An additional fluorenylmethoxycarbonyl (Fmoc) moiety in di-Fmoc-functionalized L-lysine induces pH-controlled ambidextrous gelation with significant advantages.

In recent years, several fluorenylmethoxycarbonyl (Fmoc)-functionalized amino acids and peptides have been used to construct hydrogels, which find a wide range of applications. Although several hydrogels have been prepared from mono Fmoc-functionalized amino acids, herein, we demonstrate the importance of an additional Fmoc-moiety in the hydrogelation of double Fmoc-functionalized L-lysine [Fmo...