Synthesis of 2-aminoethyl 3'-(N-glycolylneuraminyl)-β-lactoside and neoglycoconjugates based thereon - a prototype of a cancer vaccine and artificial antigens for the control of immune response

摘要

The 2-aminoethyl β-glycoside of the trisaccharide 3 '-(N-glycolylneuraminyl)lactose was synthesized in the framework of studies of approaches to the preparation of synthetic tumor vaccines based on carbohydrate chains of tumor-associated gangliosides and converted to the corresponding 2-(4-maleimidobutanoylamino)ethyl glycoside. The reaction of the latter with thiolated hemocyanin from the keyhole limpet Megathura crenulata (KLH) gave a carbohydrate-protein conjugate, a tumor vaccine prototype containing about 250 trisaccharide ligands attached to a macromolecular KLH complex. A polyvalent conjugate with a polyacryl-amide support was synthesized to be used as a coating antigen in the control of specificity and efficiency of immune response by enzyme-linked immunosorbent assay (ELISA).