1015252-19-3Relevant articles and documents
Synthesis of 3-aminopropyl β-glycoside of sialyl-3'-lactose and derived neoglycoconjugates as a tumor vaccine prototype and artificial antigens for the control of immune response
Khatuntseva,Yudina,Tsvetkov,Grachev,Stepanenko,Vlasenko,Lvov,Nifantiev
, p. 2095 - 2102 (2006)
Starting from the biotechnologically available trisaccharide sialyl-3'-lactose, representing the carbohydrate portion of the tumor-associated ganglioside GM3, the corresponding 3-aminopropyl β-glycoside (1) and 3-(4-maleimidobutanoylamino)propyl glycoside were synthesized. The reaction of the latter with a thiolated derivative of the Megathura crenulata hemocyanine (KLH) afforded a carbohydrate-protein conjugate, a tumor vaccine prototype containing about 330 trisaccharide ligands attached to KLH. N-Stearoylation of ligand 1 gave the model neoglycolipid for comparative study of the activity of mono-and polyvalent immunogens and the natural ganglioside GM3. A monovalent conjugate, in which ligand 1 is linked to biotin through an oligo(ethylene glycol) spacer and a polyvalent conjugate with a polyacrylamide carrier were also prepared. These conjugates are meant as covering antigens to assess the specificity and efficiency of the immune response in the ELISA assay.