Solid-phase synthesis of a fucosylated glycopeptide of human factor IX with a fucose-α-(1→O)-serine linkage

Abstract

The chemical synthesis of a glycopeptide with L-fucose directly linked to the hydroxy group of L-serine is reported. Two building blocks containing a protected and an unprotected fucose residue α-glycosidically linked to N^α-Fmoc-Ser-OH were prepared and used in the synthesis of a glycopeptide fragment of the EGF domain of Human Factor IX 55–65. It was demonstrated that both building blocks were completely compatible with the standard Fmoc-based solid-phase peptide synthesis protocol and furthermore that OH protection of the carbohydrate is necessary only during the final acid treatment for cleavage of the glycopeptide from the resin.