Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides.
1-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyrano se, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.
Urge
L
L
Wistar Institute of Anatomy and Biology, Philadelphia, Pennsylvania 19104.
Otvos
L
L
Lang
E
E
Wroblewski
K
K
Laczko
I
I
Hollosi
M
M
D001216:Asparagine / Q000031:analogs & derivatives*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates; D004187:Disaccharides; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data
D002241:Carbohydrates; D004187:Disaccharides; D006020:Glycopeptides; D007202:Indicators and Reagents; D001216:Asparagine