STUDIES ON 1-DEOXYNOJIRIMYCIN-CONTAINING GLYCANS - SYNTHESIS OF NOVEL DISACCHARIDES RELATED TO LACTOSE, LACTOSAMINE, AND CHITOBIOSE

被引：22

作者：

KISO, M

KATAGIRI, H

FURUI, H

HASEGAWA, A

机构：

[1] Department of Applied Bioorganic Chemistry, Gifu University

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1992年 / 11卷 / 05期

关键词：

D O I：

10.1080/07328309208016153

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：

Suitably protected 1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol; DNJ) and its 2-acetamido derivative, i.e., 2,3,6-tri-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (6) and 2-acetamido-3,6-di-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol (14) were each coupled with methyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside (15) in the presence of dimethyl(methylthio)-sulfonium triflate (DMTST) as a promoter, to give 16 and 18, which were converted to the novel disaccharides (20, 21) related to lactose and lactosamine. Coupling of 14 with methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (22) gave a chitobiose analog (25). O-(beta-D-Galactopyranosyl)-(1-->3)-DNJ derivatives (38, 39) and O-(beta-D-glucopyranosyl)-(1-->3)-DNJ (45) were also synthesized. Conformational analysis of a variety of DNJ derivatives, based on the H-1 NMR data, is also discussed.

引用

页码：627 / 644

页数：18

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