Combined Approach of Backbone Amide Linking and On-Resin N-Methylation for the 
Synthesis of Bioactive and Metabolically Stable Peptides

Wesche, Frank; Adihou, Helene; Kaiser, Astrid; Wurglics, Mario; Schubert-Zsilavecz, Manfred; Kaiser, Marcel; Bode, Helge B.

doi:10.1021/acs.jmedchem.7b01809

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Combined Approach of Backbone Amide Linking and On-Resin N-Methylation for the Synthesis of Bioactive and Metabolically Stable Peptides

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Citation

Wesche, F., Adihou, H., Kaiser, A., Wurglics, M., Schubert-Zsilavecz, M., Kaiser, M., et al. (2018). Combined Approach of Backbone Amide Linking and On-Resin N-Methylation for the Synthesis of Bioactive and Metabolically Stable Peptides. JOURNAL OF MEDICINAL CHEMISTRY, 61(9), 3930-3938. doi:10.1021/acs.jmedchem.7b01809.

Cite as: https://hdl.handle.net/21.11116/0000-000A-05B2-7

Abstract

Rhabdopeptides are a large class of nonribosomal peptides from the bacteria Xenorhabdus and Photorhabdus with low micromolar activity against different protozoa, which are the causative agents of several tropical diseases. The development of a facile and flexible synthesis combining backbone amide linking with on-resin peralkylation for the synthesis of permethylated rhabdopeptides is described. This strategy allows the fast generation of permethylated naturally occurring and artificial rhabdopeptides for a structure activity study. Furthermore, in vitro experiments revealed their superior properties regarding their stability and passive membrane diffusion.