Oligosaccharide-Peptide Ligation of Glycosyl Thiolates with Dehydropeptides: Synthesis of S-Linked Mucin-Related Glycopeptide Conjugates

Danica P. Galonić, Wilfred A. Van Der Donk, David Y. Gin

Research output: Contribution to journalArticle

Abstract

A chemoselective strategy for oligosaccharide-peptide ligation is described in which α-thio analogues of mucin-related glycoconjugates can be readily accessed through site-selective conjugate addition of complex oligosaccharide thiolates to dehydroalanine-containing peptides. The efficiency of the ligation is high-lighted by the rapid convergent assembly of thioisosteres of the four tumor-associated carbohydrate antigens, T N, T, STN, and 2,6-ST, as a pair of diastereoisomers at the newly formed cysteine stereocenter. The process proceeds in high yield and with complete retention of the α-anomeric configuration.

Original languageEnglish (US)
Pages (from-to)5997-6006
Number of pages10
JournalChemistry - A European Journal
Volume9
Issue number24
DOIs
StatePublished - Dec 15 2003

Keywords

  • Carbohydrates
  • Chemoselective ligation
  • Dehydropeptide
  • Glycopeptides
  • Mucin

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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