α-Peptide/ß-Peptoid Chimeras

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Christian Adam Olsen, Gitte Bonke, Line Vedel, Anne Adsersen, Matthias Witt, Henrik Franzyk, Jerzy W. Jaroszewski

We describe the synthesis and characterization of the first generation of oligomers consisting of alternating repeats of a-amino acids and chiral N-alkyl-ß-alanine (ß-peptoid) residues. These chimeras are stable toward proteolysis, non-hemolytic, and possess antibacterial activity comparable to well-known antimicrobial agents. Moreover, the chimeras exhibit length-dependent, concentration-dependent, solvent-dependent, and ion-strength-dependent ellipticity, indicating the presence of a secondary structure in solution. Thus, a-peptide/ß-peptoid oligomers represent a promising novel peptidomimetic backbone construct for biologically active ligands.
Original languageEnglish
JournalOrganic Letters
Volume9
Issue number8
Pages (from-to)1549–1552
Number of pages4
ISSN1523-7060
DOIs
Publication statusPublished - 2007

ID: 2432955