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-pyran-ose tautomer. The glycosidic bond geometry in (I) is stabilized by an intra-molecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except gluco-pyran-ose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I).
Highlights
The title compound, C12H24NO10+ÁClÀÁH2O, (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 -pyranose tautomer
All heteroatoms except glucopyranose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I)
Lactosamine is an important endogenous and food-related glycoepitope that provides for recognition of glycoproteins by both plant and animal -galactoside-specific lectins, such as tomato lectin (Acarin et al, 1994) or a family of mammalian galectins (Boscher et al, 2011; Mossine et al, 2008)
Summary
Lactosamine is an important endogenous and food-related glycoepitope that provides for recognition of glycoproteins by both plant and animal -galactoside-specific lectins, such as tomato lectin (Acarin et al, 1994) or a family of mammalian galectins (Boscher et al, 2011; Mossine et al, 2008). It is believed that the O10Á Á ÁH—O2 intramolecular hydrogen bond linking the two carbohydrate units is primarily responsible for stabilization of the spatial arrangement around the glycosidic bond, both in the crystal state and in solutions of Gal- 1!4-Glc diand oligosaccharides (Imberty et al 1991). This contact may be further stabilized by its involvement in multicenter hydrogen-bonding patterns. These are O1, O7, O8, and two different O1W; the chloride ions are in contact with O1, O3, O8, and O1W; the water molecules are involved in the network by serving as both donors (to Cl1 and O3) and acceptors (to two different H1A—N1—H1C groups) of strong hydrogen bonding
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