title: Solid-phase synthesis and conformational studies of glycosylated derivatives of helper-T-cell immunogenic peptides from hen-egg lysozyme.
abstract: 3-Mercaptopropionic acid and N alpha-Fmoc serine, both with unprotected carboxyl groups, were stereospecifically glycosylated in 62-82% yields, using saccharide 1,2-trans peracetates and Lewis acid catalysis. The resulting glycosylated building blocks were used in the synthesis of derivatives of helper-T-cell stimulating peptides, with the carbohydrate moiety located at the amino terminus, or internally in the peptide chain. 1H NMR spectroscopy in Me2SO-d6 showed that the glycopeptides assumed random conformations, which were not influenced by the glycosylation or by single substitutions of amino acids in the peptide moiety.
authors.affiliation: Lund Institute of Technology, Sweden.
authors.forename: M
authors.initials: M
authors.lastname: Elofsson
authors.forename: S
authors.initials: S
authors.lastname: Roy
authors.forename: B
authors.initials: B
authors.lastname: Walse
authors.forename: J
authors.initials: J
authors.lastname: Kihlberg
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D000941:Antigens / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002645:Chickens; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009113:Muramidase / Q000737:chemistry*; D010063:Ovum / Q000201:enzymology; D010446:Peptide Fragments / Q000737:chemistry*; D006377:T-Lymphocytes, Helper-Inducer / Q000276:immunology
chemical_list: D000941:Antigens; D006020:Glycopeptides; D010446:Peptide Fragments; D009113:Muramidase