A potentially valuable advance in the synthesis of carbohydrate-based anticancer vaccines through extended cycloaddition chemistry

Qian Wan, Jiehao Chen, Gong Chen, Samuel J. Danishefsky

Research output: Contribution to journalArticlepeer-review

88 Scopus citations

Abstract

An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

Original languageEnglish (US)
Pages (from-to)8244-8249
Number of pages6
JournalJournal of Organic Chemistry
Volume71
Issue number21
DOIs
StatePublished - Oct 13 2006

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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