Glycosyloxyamine neoglycosylation: A model study using calicheamicin

Randal D. Goff, Shanteri Singh, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Sweetness & light! The glycosyloxyamine glycoside of calicheamicin was exploited to form neo-D-ribosides in one efficient chemoselective step. Assessment of the neoglycosides revealed only slight reductions in cytotoxicity or ability to cleave DNA compared to the parent aglycons. This study exposes a previously unrecognized method for efficient calicheamicin bioconjugation amenable to a wide range of cancer- selective targeting modalities.

Original languageEnglish
Pages (from-to)774-776
Number of pages3
JournalChemMedChem
Volume6
Issue number5
DOIs
StatePublished - May 2 2011

Keywords

  • Carbohydrates
  • Enediynes
  • Glycosides
  • Glycosylation
  • Natural products

ASJC Scopus subject areas

  • Drug Discovery
  • General Pharmacology, Toxicology and Pharmaceutics
  • Molecular Medicine
  • Biochemistry
  • Pharmacology
  • Organic Chemistry

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