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

Oligosaccharide Synthesis on Solid, Soluble Polymer, and Tag Supports

“…43-53 A peptide synthesizer was reengineered to function as the automated oligosaccharide synthesizer and provide an easy access to structures as large as dodecasaccharides about 20 times faster than the previously reported methods. Even the oligosaccharides with branched structures are now accessible and a series of oligosaccharides of biological relevance, such as glycosylphosphatidylinositol (GPI), 54 N-glycan core pentasaccharide, 55 Lewis blood group oligosaccharides, 56 or tumor-associated antigens Gb3 and Globo-H, 57 have been prepared. Their solid-phase synthesizer uses the glycosyl phosphate building blocks and the octanediol linker attached to the resin that allow a simple automated coupling/deprotection cycle for the oligosaccharide assembly.…”

Influence of length and conformation of saccharide head groups on the mechanics of glycolipid membranes: Unraveled by off-specular neutron scattering

“…32 In the first step, the globotriaosyl trichloroacetimidate donor was synthesized. Using standard carbohydrate protecting group chemistry, 33,34 bare Gb3 was perbenzoylated, followed by anomeric deprotection and trichloroacetimidate formation. 35 In the following glycosylation reaction, globotriaosyl trichloroacetimidate ( Fig.…”

Auf dem Weg zur automatisierten Oligosaccharid‐ Synthese

“…[124] Die allgemeine Anwendbarkeit der automatisierten SPOS wurde an der Synthese eines Nonasaccharids, des Le yLe x (KH-1)-Antigenderivats 124 gezeigt (Schema 24). [125] Die Glycosylphosphate [126] Mit der automatisierten Oligosaccharidsynthese wurden verschiedene wichtige Kohlenhydrate synthetisiert, darunter das Globo-H-Hexasaccharid 133 (Schema 25), [128] das Kernpentasaccharid N-verknüpfter Glycane, [129] b-Mannosid, [130] Oligomannoside, [131] Oligorhamnoside, [132] die PhytoalexinElicitorfamilie aus Glucan [124a] und die parasitischen Impfstoffkandidaten gegen Malaria und Leishmaniose (siehe Abschnitt 7).…”

“…Die stereoselektive Gewinnung von 1,2-cis-Glycosiden bleibt eine der Hauptherausforderungen für die SPOS, obwohl es bei a-galactosidischen [128] (Schema 25) and bmannosidischen [130] Bindungen einige Fortschritte gegeben hat. Boons et al gingen dieses Problem auf elegante Art mit einer durch ein chirales Auxiliar vermittelten 1,2-cis-Gly- …”