Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the carbohydrate moiety of glycoprotein from Echinococcus granulosus have been accomplished. Trisaccharide Galβ1-3Galβ1-3GalNAcα1-R (A), tetrasaccharide Galα1-4Galβ1-3Galβ1-3GalNAcα1-R (B), and pentasaccharide Galα1-4Galβ1-3Galβ1-3Galβ1-3GalNAcα1-R (C), (R = biotinylated probe) were synthesized by stepwise condensation and/or block synthesis by the use of 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranoside as a common glycosyl acceptor. The synthesis of the tetrasaccharide and the pentasaccharide was improved from the viewpoint of reducing the number of synthetic steps and increasing the total yield by changing from stepwise condensation to block synthesis. Moreover, hexasaccharide E, which contains the oligosaccharide sequence which occurs in E. granulosus, was synthesized from trisaccharide D. We examined the antigenicity of these five oligosaccharides by an enzyme-linked immunosorbent assay (ELISA). Although compounds of C–E did not exhibit antigenicity against cystic echinococcosis (CE) patient sera, compounds B, D, and E showed good serodiagnostic potential for alveolar echinococcosis (AE).

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细粒棘球绦虫糖蛋白碳水化合物的合成及其对人血清的抗原性

已经完成了包含来自细粒棘球绦虫的糖蛋白碳水化合物部分的生物素标记寡糖部分的立体控制合成。三糖Galβ1-3Galβ1-3GalNAcα1-R( A )、四糖Galα1-4Galβ1-3Galβ1-3GalNAcα1-R( B )和五糖Galα1-4Galβ1-3Galβ1-3Galβ1-3GalNAcα1-R( C )生物化探针( C )使用 5-(甲氧基羰基)戊基 2-azido-4,6- O -benzylidene-2-deoxy-α- d通过逐步缩合和/或嵌段合成合成-吡喃半乳糖苷作为常见的糖基受体。从减少合成步骤数和提高总收率的角度改进了四糖和五糖的合成，将逐步缩合转变为嵌段合成。此外，六糖E是由三糖D合成的，其中含有E. granulosus中出现的寡糖序列。我们通过酶联免疫吸附试验 (ELISA) 检测了这五种寡糖的抗原性。尽管C - E 的化合物没有表现出针对囊性包虫病 (CE) 患者血清的抗原性，但化合物B、D和E 对肺泡型棘球蚴病 (AE) 显示出良好的血清学诊断潜力。