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An improved synthesis of a galactosylated hydroxylysine building block and its use in solid-phase glycopeptide synthesis
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
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2000 (English)In: Tetrahedron, Vol. 56, 1579-86 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2000. Vol. 56, 1579-86 p.
Keyword [en]
glycosylation, glycopeptides, solid-phase synthesis
Identifiers
URN: urn:nbn:se:umu:diva-8437DOI: doi:10.1016/S0040-4020(00)00061-2OAI: oai:DiVA.org:umu-8437DiVA: diva2:148108
Available from: 2008-01-22 Created: 2008-01-22 Last updated: 2011-01-14Bibliographically approved

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