Synthesis of the Carbohydrate Moiety of Glycoproteins from the Parasite Echinococcus granulosus and Their Antigenicity against Human Sera

Molecules

Frank Schweizer¹  Noriyasu Hada²  Takashi Ueda³  Fumiyuki Kiuchi³  Tokio Morita³  Mami Ogane³  Hiromi Nakane³  Kazuki Masuda³  Kimiaki Yamano⁴ 

[1] Department of Chemistry and Biochemistry, Faculty of Science, University of Manitoba, Winnipeg, MB R3T 2N2, Canada;Faculty of Pharmaceutical Sciences, Tokyo University of Science, Chiba 278-8510, Japan;Faculty of Pharmacy, Keio University, Tokyo 105-8512, Japan;Hokkaido Institute of Public Health, Sapporo 060-0819, Japan;

关键词: glycoprotein;    Echinococcus granulosus;    host-parasite interaction;    stereocontrolled synthesis;    biotin probe;   

DOI  :  10.3390/molecules26185652

来源: DOAJ

【 摘 要 】

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).

【 授权许可】

Unknown