Tripeptides Featuring Dehydrophenylalanine and Homophenylalanine: Homo- Versus Hetero-Chirality and Sequence Effects on Self-Assembly and Gelation

• Tipo: Artigo em Revista Científica Internacional
• Data: 2025

Autores

Carvalho, AF (Autor) Outra; Pereira, T (Autor) Outra; Oliveira, C (Autor) Outra; Figueiredo, P (Autor) Outra; Carvalho, A (Autor) Outra; David M Pereira (Autor) FFUP; L. Hilliou (Autor) Outra; Bañobre-López, M (Autor) Outra; Xu, B (Autor) Outra; Ferreira, PMT (Autor) Outra; Martins, JA (Autor) Outra

Revista

Título: GELS

Vol. 11

Página Final: 164

Indexação

ISI Web of Knowledge - 0 Citações

Scopus - 0 Citações

Outras Informações

ID Authenticus: P-018-4TK

DOI: 10.3390/gels11030164

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

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 23