Angewandte Chemie International Edition in English · 1994 · 172 citations · 17 references
Life SciencesMedicinal ChemistryPharmacologyCarbohydrate ChemistryEnzymologyStructure-activity RelationshipsEnzyme InhibitionGlycosidic Bond HydrolysisMonosaccharide ChemistryN-linked GlycosylationO-linked GlycosylationProtein GlycosylationEndoglycosidase ActivityGlycosidase ActivityGlycosidase CatalysisGlycosidase InhibitionGlycosidase InhibitorsGlycosidasesRing Atom Replacementβ-Glucosidase Activity
Replacing the anomeric C atom of 2-deoxy-O-glucose with an N atom and the ring O atom with a C atom leads to 1, the most potent β-glycosidase inhibitor known to date. This synthetic monosaccharide derivative also inhibits other glucosidases better than naturally occurring sugar derivatives in which only the O atom in the ring is exchanged for an N atom.
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Tetsuya Kajimoto, Kevin K.‐C. Liu, Richard L. Pederson et al. · Journal of the American Chemical Society · 1991 · 283 citations