Facile peptide thioester synthesis via solution-phase tosylamide preparation

Shino Manabe, Tomoyuki Sugioka, Yukishige Ito

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation.

Original languageEnglish
Pages (from-to)849-853
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number5
DOIs
Publication statusPublished - 2007 Jan 29
Externally publishedYes

Keywords

  • Glycopeptide
  • Sequential peptide ligation
  • Thioester

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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