Gels, Journal Year: 2025, Volume and Issue: 11(3), P. 164 - 164

Published: Feb. 24, 2025

Over the years, our research group developed dehydrodipeptides N-capped with aromatic moieties as protease-resistant efficacious hydrogelators, affording self-assembled hydrogels at low (critical) concentrations. Dehydrotripeptides, different dipeptide sequences and (D,L) stereochemistry, open a wider chemical space for development of soft nanomaterials. In this work, small library N-succinylated dehydrotripeptides containing C-terminal dehydrophenylalanine (∆Phe) residue scrambled sequence phenylalanine (Phe) homophenylalanine (Hph) (L-Phe-L,D-Hph L,D-Hph-L-Phe) was synthesized characterized potential hydrogelator. Two pairs diastereomeric tripeptides were synthesized, both C-protected methyl esters deprotected dicarboxylic acids. Peptides Hph-Phe-ΔPhe obtained pair (D,L,Z)/(L,L,Z) diastereomers. Their analogues Phe-Hph-ΔPhe also (L,D,Z)/(L,L,Z) pair. The effect stereochemistry (homo- vs. hetero-chirality) (Phe-∆Phe Hph-∆Phe motif) on self-assembly, biocompatibility, gelation rheological properties studied in work. Accessible, acids, are interesting molecular architectures supramolecular Interestingly, results do not comply well-documented proposition that heterochiral peptides display much higher self-assembly propensity ability than their homochiral counterparts. Further studies will be necessary to fully understand interplay between peptide homo- hetero-chirality materials.

Language: Английский