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 Academic Article uri icon

Overview

MeSH Major

  • Cysteine
  • Esters
  • Glycopeptides
  • Phenols
  • Sulfhydryl Compounds

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.

publication date

  • June 14, 2006

Research

keywords

  • Academic Article

Identity

Language

  • eng

Digital Object Identifier (DOI)

  • 10.1021/ja061588y

PubMed ID

  • 16756298

Additional Document Info

start page

  • 7460

end page

  • 2

volume

  • 128

number

  • 23