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Influence of saccharide size on the cellular immune response to glycopeptides
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
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2003 (English)In: Organic & Biomolecular Chemistry, Vol. 1, 2063-9 p.Article in journal (Refereed) Published
Abstract [en]

Glycopeptides that bind to MHC molecules on antigen presenting cells may elicit carbohydrate selective T cells. In order to investigate how the cellular immune response depends on the size of the carbohydrate moiety, a trigalactosylated derivative of an immunogenic peptide from hen egg-white lysozyme (HEL52–61) was prepared. Synthesis was accomplished by assembly of an -1,4-linked trigalactose peracetate which was coupled to Fmoc serine. After activation as a pentafluorophenyl ester the resulting building block was used in solid-phase synthesis. In contrast to the corresponding mono- and digalactosylated derivatives of HEL52–61, the trigalactosylated HEL52–61 was not immunogenic. Somewhat surprisingly, this was found to be because the trigalactosyl derivative bound approximately two orders of magnitude weaker to I-Ak MHC molecules than the mono- and digalactosyl peptides. Our observation suggests an explanation for previous findings, which show that glycopeptides isolated from MHC molecules in nature usually carry small saccharides.

Place, publisher, year, edition, pages
2003. Vol. 1, 2063-9 p.
URN: urn:nbn:se:umu:diva-9932DOI: doi:10.1039/b301747hOAI: diva2:149603
Available from: 2008-05-27 Created: 2008-05-27 Last updated: 2011-01-13Bibliographically approved

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