An improved synthesis of a galactosylated hydroxylysine building block and its use in solid-phase glycopeptide synthesis

• Different protective groups for (5R)-5-hydroxy-L-lysine were investigated in silver silicate promoted glycosylations with aceto-bromogalactose as glycosyl donor. Best results were obtained with Fmoc-Hyl(Cbz)-OAll, which was glycosylated in 80% yield. Removal of the allyl group gave a beta-D-galactosylated building block which was used in solid-phase synthesis of a glycopeptide from type II collagen. Such glycopeptides are required for studies of rheumatoid arthritis in a mouse that is transgenic for HLA-DR4, i.e. the class ii MHC molecule associated with rheumatism in humans.

Keyword

glycosylation

glycopeptides

solid-phase synthesis

Publication and Content Type

ref (subject category)

art (subject category)