Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides

Article abstract of DOI:10.1016/S0040-4039(98)02390-9

A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p- nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation of Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis.