A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid

Matthew W. Schombs, Ryan A. Davis, James C. Fettinger, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

The bridged next-generation aminoglycoside (neoglycoside), 1-deoxy-1-[(methoxy)methylamino)]-2,5-di-O-triethylsilyl-β-d- glucofuranurono-γ-lactone {systematic name: (3S,3aS,5R,6R,6aS)-5- [methoxy(methyl)amino]-3,6-bis[(triethylsilyl)oxy]-2,3,3a,5,6, 6a-hexahydrofuro[3,2-b]furan-2-one}, C20H41NO 6Si2, was synthesized in a one-pot manner from commercially available d-glucuronic acid. This structure supports the properties associated with the anomeric effect for furanosides and can be employed to provide insight into the mechanisms by which alkoxyamine-appended natural products derive their enhanced biological activity. To the best of our knowledge, this is the first published crystal structure of a bicyclic neoglycoside and is the first neoglycoside to be completely and unambiguously characterized.

Original languageEnglish (US)
Pages (from-to)1062-1066
Number of pages5
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume69
Issue number9
DOIs
StatePublished - Sep 2013

Keywords

  • crystal structure
  • neoglycoside

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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