Influence of saccharide size on the cellular immune response to glycopeptides

Mickael Mogemark, Thomas P. Cirrito, Petter Sjölin, Emil R. Unanue, Jan Kihlberg

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


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 (HEL 52-61) was prepared. Synthesis was accomplished by assembly of an α-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-Aκ 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.

Original languageEnglish
Pages (from-to)2063-2069
Number of pages7
JournalOrganic and Biomolecular Chemistry
Issue number12
StatePublished - Jun 21 2003

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