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| - Linear Synthesis of the Tumor-Associated Carbohydrate AntigensGlobo-H, SSEA-3, and Gb3
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| - The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linearfashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks wereprepared from readily available common precursors. The difficult α-(1→4-cis)-galactosidic linkagewas installed using a galactosyl phosphate donor with high selectivity. Introduction of theβ-galactosamine unit required the screening a variety of amine protecting groups to ensure gooddonor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosaminedonor performed best for the installation of the β-glycosidic linkage. Conversion of the trichloroacetylgroup to the N-acetyl group was achieved under mild conditions, fully compatible with the presenceof multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis ofthe globo-series of tumor antigens on solid-support.
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