SOLID-PHASE SYNTHESIS OF A FUCOSYLATED GLYCOPEPTIDE OF HUMAN FACTOR-IX WITH A FUCOSE-ALPHA-(1-]O)-SERINE LINKAGE

The chemical synthesis of a glycopeptide with L-fucose directly linked to the hydroxy group of L-serine is reported. Two building blocks con taining a protected and an unprotected fucose residue cc-glycosidicall y linked to N-alpha-Fmoc-Ser-OH were prepared and used in the synthesi s of a glycopeptide fragment of the EGF domain of Human Factor IX 55-6 5. It was demonstrated that both building blocks were completely compa tible with the standard Fmoc-based solid-phase peptide synthesis proto col and furthermore that OH protection of the carbohydrate is necessar y only during the final acid treatment for cleavage of the glycopeptid e from the resin.