Late-stage macrolactonisation enabled by tandem acyl transfers followed by desulphurisation

Chem Commun (Camb). 2022 Feb 24;58(17):2918-2921. doi: 10.1039/d1cc07248j.

Abstract

Intramolecular S-acylation of a thiol-installed threonine with a thioester unit, followed by S-O acyl transfer and subsequent desulphurisation, allows the synthesis of lactone peptides. A protocol has been developed enabling the cyclisation of a linear peptide, a reaction which has not been achieved by conventional methods.

MeSH terms

  • Lactones / chemistry*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Sulfhydryl Compounds / chemistry*
  • Threonine / chemistry*

Substances

  • Lactones
  • Peptides
  • Sulfhydryl Compounds
  • Threonine