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An Improved Synthesis of a Galactosylated Hydroxylysine Building Block and its use in Solid-Phase Glycopeptide Synthesis

✍ Scribed by Björn Holm; Johan Broddefalk; Sara Flodell; Eric Wellner; Jan Kihlberg

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
151 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

Different protective groups for (5R)-5-hydroxy-l-lysine were investigated in silver silicate promoted glycosylations with acetobromogalactose 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 b-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.

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