A CONVENIENT SYNTHESIS OF BETA-D-GALACTOSYL DISACCHARIDE DERIVATIVES USING THE BETA-D-GALACTOSIDASE FROM BACILLUS-CIRCULANS

被引：100

作者：

USUI, T

KUBOTA, S

OHI, H

机构：

[1] Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Shizuoka, 422

来源：

CARBOHYDRATE RESEARCH | 1993年 / 244卷 / 02期

关键词：

D O I：

10.1016/0008-6215(83)85010-1

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Beta-D-Gal-(1 --> 4)-beta-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-beta-lactosaminide) and beta-D-Gal-(1 --> 6)-beta-D-GlcNAc-OC6H4NO2-p (p-nitrophenyl N-acetyl-beta-isolactosaminide) were regioselectively synthesized from lactose and p-nitrophenyl 2-acetamido-2-deoxy-glucopyranoside, employing transglycosylation by the beta-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 beta-D-Gal-(1 --> 4)-D-GalNAc and beta-D-Gal-(1 --> 4)-beta-D-GalNAc-OC6H4NO2-p. With the enzyme, beta-D-galactosyl transfer occurred preferentially at the O-4 position of GlcNAc and GalNAc, regardless of the configuration of the hydroxyl group.

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页码：315 / 323

页数：9

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