Oligosaccharides related to xyloglucan: synthesis and X-ray crystal structure of methyl 2-0-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside

Autor: D K, Watt, D J, Brasch, D S, Larsen, L D, Melton, J, Simpson
Rok vydání: 1996
Předmět:
Zdroj: Carbohydrate research. 285
ISSN: 0008-6215
Popis: 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.
Databáze: OpenAIRE