Sugar-assisted ligation of N-linked glycopeptides with broad sequence tolerance at the ligation junction

Ashraf Brik, Simon Ficht, Yu Ying Yang, Clay S. Bennett, Chi Huey Wong

Research output: Contribution to journalArticlepeer-review

77 Scopus citations

Abstract

A novel method for the synthesis of N-linked glycopeptides using the sugar-assisted ligation strategy from cysteine free peptides is presented. The ligation junction tolerates a variety of amino acids, favoring less hindered amino acids and those with side chains that could serve as a general base in the ligation pathway. Since our approach allows the ligation of difficult junctions, the method could be applied to the synthesis of large peptides by enzymatic removal of the sugar moiety. Alternatively, more complex glycopeptides can be synthesized using glycosyltransferases. Together, this sequence of reactions should be amenable to the synthesis of glycopeptides and glycoproteins and their deglycosylated products.

Original languageEnglish
Pages (from-to)15026-15033
Number of pages8
JournalJournal of the American Chemical Society
Volume128
Issue number46
DOIs
StatePublished - 22 Nov 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Sugar-assisted ligation of N-linked glycopeptides with broad sequence tolerance at the ligation junction'. Together they form a unique fingerprint.

Cite this