Synthesis and characterisation of highly glycosylated glycopeptides with Tn-antigenic structures corresponding to human glycophorin AN.
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.
Klich
G
G
Institut für Organische Chemie, Universität Hamburg, Germany.
Paulsen
H
H
Meyer
B
B
Meldal
M
M
Bock
K
K
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
D015295:Antigens, Tumor-Associated, Carbohydrate; D002241:Carbohydrates; D006020:Glycopeptides; D006021:Glycophorins; C040286:Tn antigen