D. Watt, D. Brasch, D. Larsen
1996
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Journal
Carbohydrate research
Abstract
The disaccharides methyl 2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside and methyl 2-O-(alpha-L-fucopyranosyl)-alpha-D-galactopyranoside have been synthesised using the assisted halide reaction of tri-O-benzyl-alpha-L-fucopyranosyl bromide with methyl 3,4,6-tri-O-benzyl-beta-D-galactopyranoside and methyl 3,4,6-tri-O-benzyl-alpha-D-galactopyranoside to construct the interresidue glycosidic linkages. A crystal structure of methyl 2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside was determined using Mo-K alpha X-ray data at 183 K. The space group is P1 (No. 1) with the unit cell containing two molecules of the disaccharide with unique conformations and a water molecule. The structure was refined to R = 0.0566 for 2969 reflections. The L-fucopyranosyl and D-galactopyranosyl residues have the nominal 1C4 and 4C1 conformations, respectively. The interresidue torsion angles are comparable with those generated in a recent molecular modelling study.