Bioscience Biotechnology and Biochemistry · 2005 · 14 citations · 22 references
Life SciencesBiochemistryChemical BiologyCarbohydrate BiochemistryCarbohydrate ChemistryGlycobiologyGlycan BiosynthesisGlycan StructureGlycosylation PathwaysN-linked GlycosylationO-linked GlycosylationProtein GlycosylationDisaccharide SynthesisGlycan SynthesisGlycopeptide SynthesisGlycosyl FluoridesMucin BiologyMucin GlycoproteinsMucin-type GlycosylationSolid-phase Oligosaccharide Synthesis
The benzyl-protected disaccharide building blocks of core 8 O-glycan (15a/15b) for glycopeptide were stereoselectively synthesized by two glycosidation reactions with the glycosyl fluoride method. The building blocks were utilized in the solid-phase synthesis of a glycopeptide carrying two O-glycans with the consensus sequence of the tandem-repeat domain of MUC5AC. The synthetic glycopeptide was detached from the resin with reagent K, and subsequent debenzylation under conditions of low-acidity TfOH afforded glycopeptide 2. The synthetic sample will be used as a suitable standard in studies of the physicochemical or immunochemical characterization of mucin glycoforms.
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