title: Synthesis and characterisation of highly glycosylated glycopeptides with Tn-antigenic structures corresponding to human glycophorin AN.
abstract: Two highly glycosylated O-glycopeptides corresponding to human glycophorin AN with Tn-antigenic structures were synthesised. The first glycopeptide has two glycosylated clusters with three and six adjacent 2-acetamido-2-deoxy-D-galactose (GalNAc) glycosylation sites and represents the N-terminal octadecapeptide from Leu-1 to Lys-18. The second glycopeptide, a decapeptide from His-9 to Lys-18, contains as a compact cluster six adjacent GalNAc glycosylation sites. The solid phase synthesis was realised by using the carbohydrate-containing building blocks Fmoc-Ser(Ac3GalN3)-Pfp and Fmoc-Thr(Ac3GalN3)-Pfp. The synthesised substances were characterised by NMR spectroscopic techniques. The main techniques used were homonuclear TOCSY and NOESY as well as HMQC and HMBC for 13C,1H correlations.
authors.affiliation: Institut für Organische Chemie, Universität Hamburg, Germany.
authors.forename: G
authors.initials: G
authors.lastname: Klich
authors.forename: H
authors.initials: H
authors.lastname: Paulsen
authors.forename: B
authors.initials: B
authors.lastname: Meyer
authors.forename: M
authors.initials: M
authors.lastname: Meldal
authors.forename: K
authors.initials: K
authors.lastname: Bock
mesh_terms: D000595:Amino Acid Sequence; D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000032:analysis / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D006021:Glycophorins / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
chemical_list: D015295:Antigens, Tumor-Associated, Carbohydrate; D002241:Carbohydrates; D006020:Glycopeptides; D006021:Glycophorins; C040286:Tn antigen