Abstract
We synthesized by solution-phase methods thenaturally occurring, 10-amino acid residuelipopeptaibol antibiotics trikoningins KBI and KBII,and the [L-Iva1] KB analogue, in which the aminoacid in position 1 is different, with the aim atinvestigating the effect of hydrophobicity andchirality in that position. A solution conformationalanalysis, using FT–IR absorption and CD techniques,indicated that all of the three decapeptides arepredominantly helical in a membrane-mimeticenvironment. Permeability measurements showed anincrease of the activity from the [Aib1] peptideto the more hydrophobic [Iva1] peptides.Conversely, the effect of a change in chirality,obtained by replacing D-Iva1 with L-Iva, turnedout to be of minor significance.
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Peggion, C., Piazza, C., Formaggio, F. et al. Synthesis, conformation, and membrane modifying properties of the trikoningin KB lipopeptaibols: Effect of hydrophobicity and chirality in position 1. Letters in Peptide Science 7, 9–16 (2000). https://doi.org/10.1023/A:1008934505586
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DOI: https://doi.org/10.1023/A:1008934505586