Concise Synthesis of the Calicheamicin Oligosaccharide Using the Sulfoxide Glycosylation Method

Soong Hoon Kim, David Augeri, Dan Yang, Daniel Kahne

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Abstract

A short synthesis of the calicheamicin oligosaccharide is reported. All the glycosidic linkages have been constructed using the sulfoxide glycosylation reaction, demonstrating the efficacy of the method. A general method to introduce N-O glycosidic linkages in oligosaccharides has been developed and employed to construct the N-O bond that connects rings A and B. In the final step of the synthesis, the two halves of the calicheamicin oligosaccharide are coupled in a completely deprotected form. This convergent synthesis permits the rapid construction of derivatives of the calicheamicin oligosaccharide to test the importance of particular structural features in DNA binding.

Original languageEnglish (US)
Pages (from-to)1766-1775
Number of pages10
JournalJournal of the American Chemical Society
Volume116
Issue number5
DOIs
StatePublished - Mar 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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