Total synthesis and biological evaluation of the antibiotic lysocin E and its enantiomeric, epimeric, and N-demethylated analogues

Motoki Murai, Takuya Kaji, Takefumi Kuranaga, Hiroshi Hamamoto, Kazuhisa Sekimizu, Masayuki Inoue

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Lysocin E, a macrocyclic peptide, exhibits potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) through a novel mechanism. The first total synthesis of lysocin E was achieved by applying a full solidphase strategy. The developed approach also provides rapid access to the enantiomeric, epimeric, and N-demethylated analogues of lysocin E. Significantly, the antibacterial activity of the unnatural enantiomer was comparable to that of the natural isomer, suggesting the absence of chiral recognition in its mode of action.

Original languageEnglish
Pages (from-to)1556-1560
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number5
DOIs
Publication statusPublished - 2015 Jan 26
Externally publishedYes

Keywords

  • Antibiotics
  • Natural products
  • Solid-phase synthesis
  • Structure-activity relationships
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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