Sugar-assisted glycopeptide ligation

Ashraf Brik, Yu Ying Yang, Simon Ficht, Chi Huey Wong

Research output: Contribution to journalArticlepeer-review

112 Scopus citations

Abstract

The chemical synthesis of glycopeptides and glycoproteins from readily available materials presents an attractive route to homogeneous products for structural and functional studies. Chemical synthesis of glycopeptides and glycoproteins based on native chemical ligation represents one of the useful methods for the synthesis of natural glycopeptide structures. Here we describe a method that allows for the synthesis of glycopeptides from cysteine-free peptides. This method utilizes a peptide thioester and a glycopeptide in which the sugar moiety is modified with a thiol handle at the C-2 position. Upon completion of the ligation reaction, the thiol handle can be reduced with H2/metal to the acetamide moiety, furnishing the unmodified glycopeptides. Together, this sequence of reactions displays an attractive potential in glycopeptides and glycoproteins synthesis.

Original languageEnglish
Pages (from-to)5626-5627
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number17
DOIs
StatePublished - 3 May 2006
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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