Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcus multilocularis
Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcus multilocularis
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DOI：
10.1016/j.carres.2009.02.019
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发表时间：
2009-05-12
影响因子：
3.1
通讯作者：
Takeda, Tadahiro
中科院分区：
文献类型：
--
作者：
Koizumi, Akihiko;Hada, Noriyasu;Takeda, Tadahiro
立体控制合成了支链三糖、四糖和五糖，在多房棘球绦虫的糖蛋白抗原的糖链部分显示了Galβ1-3GalNAc核心。三糖半乳糖β1-3(GlcNAcβ1->；6)半乳糖α1-或(A)。采用嵌段合成法合成了四糖半乳糖半乳糖β1-或(Gt；3)和五糖半乳糖半乳糖α1-或(F)(R=2(三甲基硅基)乙基)。二糖2-(三甲基硅基)乙基2，3，4，6-tetra-O-acetyl-P-D-galactopyranosyl-(1->；3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside是合成支链低聚糖的常见糖基受体。采用分步缩合的方法合成了线型三糖Gal beta 1->；Gal beta 1->；3GalNacα1-OR(B)和支链四糖Gal beta 1->；3(GalNAc beta 1->；6)GalNAcα1-OR(C)。(C)2009爱思唯尔有限公司。保留所有权利。
Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Gal beta 1 -> 3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1 -> 3(GlcNAc beta 1 -> 6)GalNAc alpha 1-OR (A). tetrasaccharide Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 6)GalNac alpha 1-OR(D), and pentasaccharides Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 4Gl cNAc beta 1-6)GalNAc alpha 1-OR (E) and Gal beta 1-3(Gal alpha 1 -> 4Gal alpha 1 -> 4Gal alpha 1 -> 6)GalNAc alpha 1-OR) (F) (R = 2(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-P-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharicles. Moreover, linear trisaccharide Gal beta 1 -> Gal beta 1 -> 3GalNac alpha 1-OR (B) and branched tetrasaccharide Gal beta 1 -> Gal beta 1 -> 3(GalNac beta 1 -> 6)GalNac alpha 1-OR (C) were synthesized by stepwise condensation. (C) 2009 Elsevier Ltd. All rights reserved.