ABSTRACT
The crystal structure of the title compound, C18H24N2O11, a GalNAc mimic containing an alpha-glycosyloxysuccinimide linkage, has been determined. The pyranose ring geometry is an almost perfect (4)C(1) chair. The torsion angle of the exocyclic hydroxymethyl group is shown to be gauche-trans with respect to O1 and C4, respectively.
Subject(s)
Galactosamine/chemistry , Galactose/analogs & derivatives , Succinimides/chemistry , Acetylgalactosamine/chemistry , Carbohydrate Conformation , Galactosamine/analogs & derivatives , Molecular Mimicry , Molecular StructureABSTRACT
The crystalline-state conformation of the title compound, C(29)H(29)NO(9), has been established unequivocally. The R absolute configuration is observed at the 4-methoxyamino moiety and the pyranose ring adopts essentially a perfect (4)C(1) chair. The torsion angle of the exocyclic hydroxymethyl group is shown to be gauche--gauche with respect to O1 and C4, respectively. The conformation along the methoxyamino bond is consistent with that observed for calicheamicin gamma(1)(I).
