Direct on-resin synthesis of peptide-αthiophenylesters for use in native chemical ligation

Duhee Bang, Brad L. Pentelute, Zachary P. Gates, Stephen B. Kent

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A peptide-αthiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-αthiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-αthiophenylesters using a simple and efficient method. The peptide- αthiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-αthioalkylester.

Original languageEnglish
Pages (from-to)1049-1052
Number of pages4
JournalOrganic Letters
Volume8
Issue number6
DOIs
Publication statusPublished - 2006 Mar 16

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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