Crystal Structure of Methyl 3-O-α-d-Glucopyranosyl 2-Acetamido-2-Deoxy-α-d-Galactopyranoside Hydrate

Methyl 3-O-α-d-glucopyranosyl 2-acetamido-2-deoxy-α-d-galactopyranoside as a monohydrate, C₁₅H₂₇NO₁₁·H₂O, crystallizes in space group P2₁2₁2₁, with four molecules in the unit cell. It constitutes the methyl glycoside of the carbohydrate part of the teichoic acid type polysaccharide from Micrococcus sp. A1, in which the disaccharides are joined through phosphodiester linkages. The conformation of the disaccharide is described by the glycosidic torsion angles ϕ =  − 31° and ψ =  + 1°, and the hydroxymethyl groups of the constituent monosaccharides are present in the gg and gt conformations for the sugar residues having the gluco- and galacto-configuration, respectively. For the N-acetyl group at C2 of the galactosamine residue the torsion angle τ_H = 147°, i.e., the amide proton has an antiperiplanar relationship to H2 of the sugar ring. The structure shows extensive hydrogen bonding along the a-direction, including the water molecule, and forms sheets with hydrophilic interactions within the sheets as a result of hydrogen bonding between disaccharides as well as hydrophobic interactions between the sheets, in particular, amongst methyl groups of the N-acetyl group of the α-d-GalpNAc residue in the disaccharides.

Graphical Abstract

The structure of the title disaccharide as a monohydrate, C₁₅H₂₇NO₁₁·H₂O, which shows extensive hydrogen bonding as well as hydrophobic interactions, was determined from minute crystals using synchrotron radiation and verified by solid state DFT calculations using plane waves.