Synthesis of a 2‐arylsulphonylated tryptophan: the antibacterial activity of bovine lactoferricin peptides containing Trp(2‐Pmc)

A modified tryptophan, β‐[2‐(2,2,5,7,8‐pentamethylchroman‐6‐sulphonyl)‐indol‐3‐yl]alanine, Trp(2 − Pmc) = Tpc has been synthesized. Replacement of tryptophan in a bovine lactoferricin model peptide with the modified tryptophan resulted in peptides with a substantially increased antibacterial activity against Escherichia coli and Staphylococcus aureus. The most active peptides against each bacterial strain displayed minimal inhibitory concentrations of 7.5 μg/ml. Copyright © 2002 European Peptide Society and John Wiley & Sons, Ltd.

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