Synthesis and binding to plant lectins of sulfur-containing analogues of βGal1,3αGalNAc (T-antigen)

Analogues of the tumor-associated T-antigen (βGal1,3αGalNAc) containing 4,6-epidithio and 4,6-thietan modifications were synthesized from the α-allyl glycoside of βGalα1,3G1cNAc via suitable thiocyanate derivatives. Binding to three leguminous lectins as model systems was investigated in an enzyme-linked lectin assay (ELLA) and IC50 values comparable to the corresponding natural disaccharides T-antigen, lactose and N-acetyllactosamine were found.