Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis.
N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carrying O-glycosidically alpha- or beta-linked peracetylated beta-D-Galp-(1-3)-D-GalNAcp carbohydrate chains, were prepared. These derivatives are intended for use in solid phase glycopeptide synthesis. Suitably protected mono- and disaccharide thioglycosides were used as carbohydrate intermediates. These were activated by treatment with bromine to give the glycosyl bromides, which were then used in silver triflate-promoted glycosidations of N-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids.
Lüning
B
B
Department of Organic Chemistry, University of Stockholm, Sweden.
Norberg
T
T
Tejbrant
J
J
D000596:Amino Acids; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides; D006020:Glycopeptides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009005:Monosaccharides; D009904:Optical Rotation; D010455:Peptides / Q000138:chemical synthesis*
D000596:Amino Acids; D004187:Disaccharides; D006020:Glycopeptides; D007202:Indicators and Reagents; D009005:Monosaccharides; D010455:Peptides