Solid-phase synthesis of complex oligosaccharides using a novel capping reagent.
Solid-phase-supported oligosaccharide synthesis of a core N-glycan tetrasaccharide and of a trisaccharide containing the Galili antigen is reported. The synthesis is based on a hydroxymethylbenzyl benzoate spacer-linker system attached to the Merrifield resin, O-Fmoc-protected O-glycosyl trichloroacetimidates as glycosyl donors, and benzoyl isocyanate as a capping reagent for low-reactivity hydroxy groups. In this way, the target molecules could be efficiently obtained with little byproduct formation, and hence final purification was convenient.
Wu
Xiangyang
X
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Schmidt
Richard R
RR
D000081:Acetamides; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry; D014238:Trichloroacetic Acid / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis
D000081:Acetamides; D062845:Chloroacetates; D009844:Oligosaccharides; D011134:Polysaccharides; D014312:Trisaccharides; D014238:Trichloroacetic Acid; C009528:trichloroacetamide