Obviation of hydrogen fluoride in Boc chemistry solid phase peptide synthesis of peptide-αthioesters

Chem Commun (Camb). 2016 Nov 29;52(97):13979-13982. doi: 10.1039/c6cc07891e.

Abstract

Under suitable conditions, trifluoromethanesulfonic acid performs comparably to hydrogen fluoride for the on-resin global deprotection of peptides prepared by Boc chemistry solid phase peptide synthesis (SPPS). Obviation of hydrogen fluoride in Boc chemistry SPPS enables the straightforward synthesis of peptide-αthioesters for use in native chemical ligation.

MeSH terms

  • Amino Acid Sequence
  • Esters / chemistry*
  • Hydrofluoric Acid / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Solid-Phase Synthesis Techniques

Substances

  • Esters
  • Peptides
  • Hydrofluoric Acid