AUTOMATED SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDES - INCORPORATION OF UNPROTECTED MONOSACCHARIDE AND DISACCHARIDE UNITS OF N-GLYCOPROTEIN ANTENNAE INTO T-CELL EPITOPIC PEPTIDES

A new reagent for custom synthesis of N-glycosylated peptides, Fmoc-Asn[GlcNAc(1»4)-GlcNAc]-OH, has been prepared. The O-glycosidic bond survived the trifluoroacetic acid cleavage. High coupling efficiencies were obtained when this glycoamino acid derivative was used for solid-phase synthesis of a test peptide and a T cell epitopic dodecapeptide containing an Asn residue in mid-chain position. An automated peptide synthesizer was used to produce the parent Asn peptide and its N-acetyl-glycosyl mono- and disaccharide derivatives. © 1990.