ABSTRACT
The syntheses of various fluorinated MUC1 glycopeptide antigens and their specific binding to serum antibodies from mice immunized with natural and fluorinated TF(6)-MUC1-TTox conjugate vaccines are presented.
Subject(s)
Antibodies/chemistry , Antigens/chemistry , Glycopeptides/chemistry , Mucin-1/chemistry , Animals , Antibodies/blood , Antibodies/immunology , Antigen-Antibody Reactions , Antigens/immunology , Glycopeptides/chemical synthesis , Glycopeptides/immunology , Mice , Mucin-1/immunologyABSTRACT
Selectively 6-fluorinated analogs of the tumor-associated T(N) antigen Fmoc-Thr(α-O-GalNAc)-OtBu can be efficiently prepared using DAST-mediated de(hydr)oxyfluorination reactions of preformed and orthogonally protected glycosyl amino esters without affecting the labile protecting groups and O-glycosidic linkages. The resulting mono- and difluorinated T(N) analogs are interesting building blocks for non-hydrolyzable mucin-type antigen mimetics, as illustrated by the unprecedented synthesis of two different multiply fluorinated Thomsen-Friedenreich derivatives. The reported deoxyfluoro antigen analogs represent important functional probes for carbohydrate-binding proteins and glycosyl-processing enzymes.
