Carbohydrate Research p. 315 - 323 (1993)
Update date:2022-08-05
Topics:
Usui
Kubota
Ohi
β-D-Gal-(1 → 4)-β-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-β-lactosaminide) and β-D-Gal-(1 → 6)-β-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-β-isolactosaminide) were regioselectively synthesized from lactose and p-nitrophenyl 2-acetamido-2-deoxy-glucopyranoside, employing transglycosylation by the β-D-galactosidase from Bacillus circulans and by controlling the concentration of organic solvent in the reaction system. The (1 → 4)-linked disaccharide was formed exclusively when the concentration of organic solvent was high, whereas the (1 → 6)-linked isomer was produced with a low concentration. Further utilization of the transglycosylation by the enzyme led to the regioselective formation of β-D-Gal-(1 → 4)-D-GalNAc and β-D-Gal-(1 → 4)-β-D-GalNAc-OC6H4NO2-p. With the enzyme, β-D-galactosyl transfer occurred preferentially at the O-4 position of GlcNAc and GalNAc, regardless of the configuration of the hydroxyl group. β-D-Gal-(1→4)-b-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-β-lactosaminide) and β-D-Gal-(1→6)-β-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-β-isolactosaminde) were regioselectively synthesized from lactose and p-nitrophenyl 2-acetamido-2-deoxy-glucopyranoside, employing transglycosylation by the b-D-galactosidas from Bacillus circulans and by controlling the concentration of organic solvent in the reaction system. The (1→4) linked disaccharide was formed exclusively when the concentration of organic solvent was high, whereas the (1→6)-linked isomer was produced with a low concentration. Further utilization of the transglycosylation by the enzyme led to the regioselective formation of β-D-Gal-(1→4)-D-GalNAc and β-D-Gal-(1→4)-β-D-GalNAc-OC6H4NO2-p. With the enzyme, β-D-galactosyl transfer occurred preferentially at the O-4 position of GlcNAc, regardless of the configuration of the hydroxyl group.
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