Synthesis of fluorinated Thomsen-Friedenreich antigens: direct deoxyfluorination of αGalNAc-threonine tert-butyl esters

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-glycos...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-08, Vol.9 (15), p.5541-5546
Main Authors: Johannes, Manuel, Oberbillig, Thomas, Hoffmann-Röder, Anja
Format: Article
Language:English
Subjects:
Acetylgalactosamine - chemistry
Antigens, Tumor-Associated, Carbohydrate - chemistry
Fluorescent Dyes - chemistry
Fluorine - chemistry
Threonine - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob05373f