α-Peptide/ß-Peptoid Chimeras

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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