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

Org Lett. 2006 Mar 16;8(6):1049-52. doi: 10.1021/ol052811j.

Abstract

[reaction: see text] A peptide-(alpha)thiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-(alpha)thiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-(alpha)thiophenylesters using a simple and efficient method. The peptide-(alpha)thiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-(alpha)thioalkylester.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Esters
  • Models, Molecular
  • Molecular Sequence Data
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Thermodynamics

Substances

  • Benzene Derivatives
  • Esters
  • Peptides