6533b86efe1ef96bd12cb56e
RESEARCH PRODUCT
Synthesis of fluorinated Thomsen-Friedenreich antigens: direct deoxyfluorination of αGalNAc-threonine tert-butyl esters.
Manuel JohannesThomas OberbilligThomas OberbilligAnja Hoffmann-rödersubject
chemistry.chemical_classificationTert butylThreonineAcetylgalactosamineAmino estersCarbohydrate chemistryStereochemistryOrganic ChemistryFluorineBiochemistrychemistry.chemical_compoundEnzymechemistryAntigenGlycosylAntigens Tumor-Associated CarbohydratePhysical and Theoretical ChemistryThreonineFluorescent Dyesdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-06-23 | Organicbiomolecular chemistry |