title: 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-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 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.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA.
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Schombs
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Davis
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D020723:Glucuronic Acid / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D006027:Glycosides; D007783:Lactones; D020723:Glucuronic Acid
keywords: crystal structure; neoglycoside