Facile and mild synthesis of linear and cyclic peptides via thioesters

Org Lett. 2014 Aug 1;16(15):3922-5. doi: 10.1021/ol501669n. Epub 2014 Jul 17.

Abstract

Thioester-mediated peptide bond formation has recently garnered a lot of attention, most notably in its relevance to condensation of large peptide fragments. Herein, a simple and general ligation method for the preparation of linear and cyclic peptides, starting from peptide thioester, mainly p-chlorophenyl, precursors is reported. The inherent advantages of this method are the low epimerization, reduced dimerization, use of mild reaction conditions, and elimination of superfluous coupling reagents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Esters
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Sulfur Compounds / chemistry*

Substances

  • Esters
  • Peptides
  • Peptides, Cyclic
  • Sulfur Compounds