β-d-Galactopyranosyl-(1→4)–2-amino-2-deoxy-α-d-glucopyranose hydrochloride monohydrate (lactosamine)

Abstract

The title compound, C12H24NO10+·Cl−·H2O, (I), crystallizes in the monoclinic space group P21 and exists as a monohydrate of a monosubstituted ammonium chloride salt, with the reducing carbohydrate portion existing exclusively as the α-pyranose tautomer. The glycosidic bond geometry in (I) is stabilized by an intramolecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except glucopyranose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I).

Keywords

• crystal structure
• glycosidic bond geometry
• heyns rearrangement
• hydrogen bonding