6533b858fe1ef96bd12b6cea
RESEARCH PRODUCT
Synthesis of glycopeptides and neoglycoproteins containing the fucosylated linkage region of N-glycoproteins.
Horst KunzCarlo Unverzagtsubject
Magnetic Resonance SpectroscopyGlycoconjugateClinical BiochemistryMolecular Sequence DataPharmaceutical SciencePeptideChitobioseDisaccharidesBiochemistryFucosechemistry.chemical_compoundViral ProteinsViral envelopeDrug DiscoveryAsparagineAmino Acid SequenceBovine serum albuminMolecular BiologyGlucansFucoseGlycoproteinschemistry.chemical_classificationbiologyOrganic ChemistryGlycopeptidesFucosyltransferasesGlycopeptidechemistryBiochemistryCarbohydrate Sequencebiology.proteinMolecular MedicineAsparaginedescription
Abstract N-Glycoproteins fucosylated in the core region occur in tumor membranes and virus envelopes. Partial structures of such N-glycoproteins containing fucosylated chitobiosyl asparagine conjugates were synthesized using the allyloxycarbonyl (Aloc) and the tert-butyl ester protecting groups in the peptide portion. As the α-fucosidic bond of the conjugates revealed to be very sensitive to acids when carrying ether-type protecting groups, a method for exchanging the protecting groups of the fucose portion of saccharides was developed. Conjugates containing O-acetyl protected fucose proved to be stable against acids used in glycopeptide syntheses. These methods were applied in the synthesis of a fucosyl chitobiose hexapeptide with the partial sequence of a leukemia virus envelope glycoprotein. The glycopeptide was coupled to bovine serum albumin yielding a neoglycoprotein which contains a glycoconjugate of exactly specified structure.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1994-11-01 | Bioorganicmedicinal chemistry |