Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines

Org Lett. 2019 Apr 5;21(7):2200-2203. doi: 10.1021/acs.orglett.9b00125. Epub 2019 Mar 11.

Abstract

Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Amino Acids / chemistry*
  • Aziridines / chemistry*
  • Gram-Positive Bacteria / chemistry
  • Gram-Positive Bacteria / drug effects*
  • Indium / chemistry*
  • Molecular Structure
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry

Substances

  • Amino Acids
  • Aziridines
  • Sulfides
  • Indium
  • beta-methyllanthionine
  • Alanine