Automated Synthesis of the Tumor-Associated Carbohydrate Antigens Gb-3 and Globo-H:  Incorporation of α-Galactosidic Linkages

The Globo series of tumor-associated antigens are glycosphingolipids implicated in several cancer types. These oligosaccharides contain an α-linked galactose. Reported are methods to efficiently install cis-galactosidic linkages by automated solid-phase oligosaccharide synthesis. The complex tumor-associated oligosaccharides Globo-H and Gb-3 were assembled in about 1 day using the new approach that extends the scope of automated oligosaccharide synthesis to structurally more challenging carbohydrates.