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α-peptide/β-peptoid chimeras

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ORGANIC LETTERS
卷 9, 期 8, 页码 1549-1552

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AMER CHEMICAL SOC
DOI: 10.1021/ol070316c

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[GRAPHICS] 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.

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