Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides

Gong Chen, J. David Warren, Jiehao Chen, Bin Wu, Qian Wan, Samuel J. Danishefsky

Research output: Contribution to journalArticle

52 Scopus citations

Abstract

A pathway has been devised, wherein a phenolic ester of a C-terminal peptide is ligated with an N-terminal peptide through two consecutive acyl migrations. In the first transacylation, the C-terminus is transferred from a phenol to a newly liberated ortho-thiol function. Subsequently, the acyl group is transported to a proximal benzylamine through a six-membered transition state.

Original languageEnglish (US)
Pages (from-to)7460-7462
Number of pages3
JournalJournal of the American Chemical Society
Volume128
Issue number23
DOIs
StatePublished - Jun 14 2006

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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