6533b85afe1ef96bd12b8d23

RESEARCH PRODUCT

Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis

Horst KunzAlexander Rösch

subject

GlycosylationAnomerStereochemistryMolecular Sequence DataOligosaccharidesBiochemistryAnalytical Chemistrychemistry.chemical_compoundLewis Blood Group AntigensAsparagineTrisaccharideNuclear Magnetic Resonance Biomolecularchemistry.chemical_classificationChemistryOrganic ChemistryGlycopeptidesRegioselectivityStereoisomerismGeneral MedicineGlycopeptideCarbohydrate SequenceAzideAsparagineOligopeptidesFluorideLinker

description

Using the stannylene method, the trisaccharide 2-acetamido-3-O-[6-O-benzyl-beta-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-beta-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide was regioselectively sulfonated and, after reduction of the anomeric azide, coupled to Fmoc alpha-allyl aspartate. After Pd(0)-catalyzed deallylation, the sulfatyl Lewis(a) asparagine building block was obtained, suitable for solid-phase glycopeptide synthesis applying the fluoride labile PTMSEL linker system.

yearjournalcountryeditionlanguage
2006-01-19Carbohydrate Research
https://doi.org/10.1016/j.carres.2006.03.003