Macrolactonization of peptide thioesters catalyzed by imidazole and its application in the synthesis of kahalalide B and analogues

Org Lett. 2010 May 21;12(10):2250-3. doi: 10.1021/ol100596p.

Abstract

The macrolactonization of peptide thioester to yield cyclic depsipeptides was developed using imidazole as a catalyst. This strategy was applied to the synthesis of kahalalide B and its analogues.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Imidazoles / chemistry*
  • Lactones / chemistry*
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Depsipeptides
  • Imidazoles
  • Lactones
  • Peptides, Cyclic
  • Sulfhydryl Compounds
  • kahalalide B
  • imidazole