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).

中文翻译：

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细粒棘球绦虫寄生虫糖蛋白碳水化合物部分的合成及其对人血清的抗原性


含有细粒棘球绦虫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已经完成。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 )，（R = 生物素化探针）使用5-(甲氧基羰基)戊基2-叠氮基-4,6- O-亚苄基-2-脱氧-α- d-吡喃半乳糖苷作为常见糖基受体，通过逐步缩合和/或嵌段合成法合成。通过从逐步缩合变为嵌段合成，从减少合成步骤数和增加总收率的角度来看，改进了四糖和五糖的合成。此外，由三糖D合成了六糖E ，其含有细粒棘球绦虫中存在的寡糖序列。我们通过酶联免疫吸附测定（ELISA）检查了这五种寡糖的抗原性。虽然C – E化合物对囊性包虫病 (CE) 患者血清不表现出抗原性，但化合物B 、 D和E对肺泡型包虫病 (AE) 显示出良好的血清诊断潜力。