Solid supported chemical syntheses of both components of the lantibiotic lacticin 3147

Wei Liu, Alice S H Chan, Hongqiang Liu, Stephen A Cochrane, John C Vederas

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)

Abstract

Lantibiotics are antimicrobial peptides produced by bacteria. Some are employed for food preservation, whereas others have therapeutic potential due to their activity against organisms resistant to current antibiotics. They are ribosomally synthesized and posttranslationally modified by dehydration of serine and threonine residues followed by attack of thiols of cysteines to form monosulfide lanthionine and methyllanthionine rings, respectively. Chemical synthesis of peptide analogues is a powerful method to verify stereochemistry and access structure-activity relationships. However, solid supported synthesis of lantibiotics has been difficult due to problems in generating lanthionines and methyllanthionines with orthogonal protection and good stereochemical control. We report the solid-phase syntheses of both peptides of a two-component lantibiotic, lacticin 3147. Both successive and interlocking ring systems were synthesized on-resin, thereby providing a general methodology for this family of natural products.

Original languageEnglish
Pages (from-to)14216-9
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number36
DOIs
Publication statusPublished - 14 Sep 2011

Keywords

  • Amino Acid Sequence
  • Bacteriocins
  • Molecular Sequence Data
  • Structure-Activity Relationship
  • Journal Article
  • Research Support, Non-U.S. Gov't

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