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 Citation (Scopus)

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

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Glucuronic Acid
Aminoglycosides
Lactones
Bioactivity
Biological Products
Names
Crystal structure

Keywords

  • crystal structure
  • neoglycoside

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid. / Schombs, Matthew W.; Davis, Ryan A.; Fettinger, James C.; Gervay-Hague, Jacquelyn.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 69, No. 9, 09.2013, p. 1062-1066.

Research output: Contribution to journalArticle

Schombs, Matthew W. ; Davis, Ryan A. ; Fettinger, James C. ; Gervay-Hague, Jacquelyn. / A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid. In: Acta Crystallographica Section C: Crystal Structure Communications. 2013 ; Vol. 69, No. 9. pp. 1062-1066.
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