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

ABSTRACT: The bridged next-generation aminoglycoside (neoglycoside), 1-deoxy-1-[(methoxy)methylamino)]-2,5-di-O-triethylsilyl-?-D-glucofuranurono-?-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}, C20H41NO6Si2, 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.

SUBMITTER: Schombs MW

PROVIDER: S-EPMC3769141 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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

Schombs Matthew W MW Davis Ryan A RA Fettinger James C JC Gervay-Hague Jacquelyn J

Acta crystallographica. Section C, Crystal structure communications 20130807 Pt 9

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}, C20H41NO6Si2, 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 provi ...[more]

PMID: 24005522

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