Stereocontrolled synthesis of sulfur-linked analogues of the branched tetrasaccharide repeating-unit of the immunostimulant polysaccharide schizophyllan and of its beta-(1->3)-branched, beta-(1->6)-linked isomer

被引：14

作者：

ContourGalcera, MO

Ding, YL

OrtizMellet, C

Defaye, J

机构：

[1] CTR ETUD GRENOBLE,CNRS,F-38041 GRENOBLE,FRANCE

[2] CTR ETUD GRENOBLE,CEA,DEPT RECH FONDAMENTALE MAT CONDENSEE,SESAM,F-38041 GRENOBLE,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1996年 / 281卷 / 01期

关键词：

sulfur-linked thiooligosaccharides; schizophyllan tetrasaccharide repeating-unit thio analogue; immunostimulant polysaccharide repeating-unit thio analogue; phytoalexin elicitor repeating-unit thio analogue;

D O I：

10.1016/0008-6215(95)00334-7

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：

The branched, sulfur-linked tetrasaccharide S-(beta-D-glucopyranosyl)-(1 --> 3)-S-[(6-S-beta-D-glucopyranosyl)-3,6-dithio-beta-D-glucopyranosyl]-(1 --> 3)-S-3-thio-D-glucopyranose (9) has been conveniently prepared by S(N)2 displacement of the triflate group in 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-allofuranose with the sodium salt of 2,4-di-O-acetyl-3,6-di-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)- 1,3,6-trithio-beta-D-glucopyranose (5). Conversely, reaction of the sodium salt of 5 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-beta-D-glucopyranose afforded the positional isomer S-(beta-D-glucopyranosyl)-(1 --> 6)-S-[(3-S-beta-D-glucopyranosyl)-3,6-dithio-beta-D-glucopyranosyl]-(1 --> 6)-S-6-thio-D-glucopyranose (12).

引用

页码：119 / 128

页数：10

共 16 条

[1] OLIGOSACCHARINS - OLIGOSACCHARIDE REGULATORY MOLECULES [J].