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Bioorg Med Chem. 2000 Apr;8(4):833-9.

Design and synthesis of novel antimicrobial pseudopeptides with selective membrane-perturbation activity.

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  • 1Protein Chemistry Laboratory, Mogam Biotechnology Research Institute, Yongin-City, Kyonggi-Do, South Korea.


By incorporating carbamate bond(s) into a cytolytic peptide, novel pseudopeptides with potent antibacterial activity and low hemolytic activity were synthesized. Circular dichroism spectra suggested that the incorporation of carbamate bond(s) decrease the alpha helical conformation of the peptide in lipid membrane circumstances, which must be regarded as a major factor for the separation of antibacterial activity from cytotoxic activity for mammalian cell. Experiments in which dye was released from vesicles indicated that the potent antibacterial activity and low hemolytic activity of the pseudopeptides must be due to their great lipid membrane selectivity. The present result suggest that backbone modifications can be a great tool for developing pseudopeptides with improved biological activity and bioavailability from cytolytic peptides.

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