Synthesis of glycosylated hydroxyproline building blocks

Abstract

The synthesis of a series of new glycosylated Nα-Fmoc hydroxyproline building blocks has been accomplished for the first time with two approaches. First, by glycosylation of Nα-Fmoc Hyp OH, having unprotected carboxyl group with different peracetylated glycosyl derivatives. Alternatively, by glycosylation of its derivative Nα-Fmoc Hyp Opfp with different acylated glycosyl derivatives under silver triflate promotion. The use of benzoyl groups instead of acetyl as protecting groups for the carbohydrate moiety boosted the yield of glycosidation of Nα-Fmoc Hyp Opfp. These building blocks are ready for their incorporation into solid-phase glycopeptide synthesis protocols. © 1995.