Enzymatic Syntheses of N -Acetyllactosamine and N -Acetylallolactosamine by the Use of β-D-Galactosidases

作者：Kazuo Sakai, Ryosuke Katsumi, Hiroshi Ohi, Taichi Usui, Yoshiharu Ishido · 发表于：Journal of Carbohydrate Chemistry · 年份：1992 · DOI：10.1080/07328309208016148 · 被引用次数：96 · 研究领域：Enzyme Production and Characterization、Carbohydrate Chemistry and Synthesis、Enzyme Catalysis and Immobilization

A β-D-galactosidase from Bacillus circulans induced β-D-galactopyranosyl transfer from lactose predominantly to a secondary (OH-4) rather than the primary hydroxyl group (OH-6) of 2-acetamido-2-deoxy-D-glucopyranose. 4-O-β-D-Galacto-pyranosyl-2-acetamido-2-deoxy-D-glucopyranose (N-acetyl-lactosamine) was thus readily synthesized on a gram scale and conveniently isolated by chromatography on a column of charcoal-Celite. On the other hand, the glycosyl transfer to the 6-position predominantly was efficiently induced to give 6-O-β-D-galactopyranosyl-2-acetamido-2-deoxy-D-glucopyranose (N-acetyl-allolactosamine) by consecutive use of β-D-galactosidases from Kluyveromyces lactis and B. circulans. These enzyme reactions were efficient enough to allow the one-pot preparation of the desired disaccharides.