Alpha-peptide/beta-peptoid chimeras.
[structure: see text] We describe the synthesis and characterization of the first generation of oligomers consisting of alternating repeats of alpha-amino acids and chiral N-alkyl-beta-alanine (beta-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, alpha-peptide/beta-peptoid oligomers represent a promising novel peptidomimetic backbone construct for biologically active ligands.
Olsen
Christian A
CA
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark. cao@farma.ku.dk
Bonke
Gitte
G
Vedel
Line
L
Adsersen
Anne
A
Witt
Matthias
M
Franzyk
Henrik
H
Jaroszewski
Jerzy W
JW
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002942:Circular Dichroism; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D010455:Peptides; D034444:Peptoids