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Sie sind hier: Startseite AK Hansen Publikationen Hybrid Peptides Based on α‐Aminoxy Acids as Antimicrobial and Anticancer Foldamers

Laura Sinatra, Lisa Kolano, Maik Icker, Stefan R Fritzsche, Daniela Volke, Ines Gockel, René Thieme, Ralf Hoffmann, and Finn K Hansen (2021)

Hybrid Peptides Based on α‐Aminoxy Acids as Antimicrobial and Anticancer Foldamers

ChemPlusChem, 86(6):827–835.

α-Aminoxy peptides represent an interesting group of peptidomimetics with high proteolytic stability and the ability to fold into specific, predictable secondary structures. Here, we present a series of hybrid peptides consisting of α-aminoxy acids and α-amino acids with cationic and aromatic, hydrophobic side chains in an alternating manner synthesized using an efficient protocol that combines solution- and solid-phase synthesis. 2D ROESY experiments with a representative hexamer suggested the presence of a 7/8 helical conformation in solution. Biological evaluation revealed a significant impact of the peptide chain length and the N-terminal cap on the antimicrobial and anticancer properties of this series of hybrid peptides. The Fmoc-capped peptide 6e displayed the most potent antimicrobial activity against a panel of Gram-negative and Gram-positive bacterial strains (e. g. against E. Coli: MIC=8 mg/L; S. aureus: MIC=4 mg/L).

anticancer peptides, antimicrobial activity, foldamers, peptidomimetics, α-aminoxy acids