Chemical synthesis and biological activity of analogues of the lantibiotic epilancin 15X

Patrick J. Knerr, Wilfred A. Van Der Donk

Research output: Contribution to journalArticlepeer-review

Abstract

Lantibiotics are a large family of antibacterial peptide natural products containing multiple post-translational modifications, including the thioether structures lanthionine and methyllanthionine. Efforts to probe structure-activity relationships and engineer improved pharmacological properties have driven the development of new methods to produce non-natural analogues of these compounds. In this study, solid-supported chemical synthesis was used to produce analogues of the potent lantibiotic epilancin 15X, in order to assess the importance of several N-terminal post-translational modifications for biological activity. Surprisingly, substitution of these moieties, including the unusual N-terminal d-lactyl moiety, resulted in relatively small changes in the antimicrobial activity and pore-forming ability of the peptides.

Original languageEnglish (US)
Pages (from-to)7648-7651
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number18
DOIs
StatePublished - May 9 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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