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Chemoenzymatic synthesis of derivatives of a T-cell-stimulating peptide which carry tumor-associated carbohydrate antigens
Umeå University, Faculty of Science and Technology, Chemistry.
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2001 (English)In: Journal of the Chemical Society-Perkin Transactions 1, 880-5 p.Article in journal (Refereed) Published
Abstract [en]

The Tn (GalNAc-Ser/Thr), T [Gal(13)GalNAc-Ser/Thr], sialyl-Tn [Neu5Ac(26)GalNAc-Ser/Thr] and 2,3-sialyl-T [Neu5Ac(23)Gal(13)GalNAc-Ser/Thr] antigens are examples of tumor-associated carbohydrate antigens expressed by epithelial cancers. We now describe the preparation of 2-bromoethyl glycosides corresponding to the Tn and T antigens in one and five chemical steps (51 and 15% total yield), respectively, starting from N-acetylgalactosamine. The 2-bromoethyl Tn and T glycosides were used to alkylate a homocysteine residue incorporated in a peptide that is able to bind to class I MHC molecules on antigen-presenting cells. The two neoglycopeptides were then converted into glycopeptides which carry the sialyl-Tn and 2,3-sialyl-T antigens by using recombinant sialyltransferases. Interestingly, the sialyltransferases were able to sialylate the Tn and T carbohydrate moieties even though they were linked to the peptide backbone via a spacer instead of being attached to serine or threonine. The four glycopeptides will be used in studies directed towards inducing a carbohydrate-specific T cell response against the Tn, T, sialyl-Tn, and 2,3-sialyl-T antigens.

Place, publisher, year, edition, pages
2001. 880-5 p.
URN: urn:nbn:se:umu:diva-9578DOI: doi:10.1039/b009567mOAI: diva2:149249
Available from: 2008-04-28 Created: 2008-04-28 Last updated: 2011-01-13Bibliographically approved

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Kihlberg, Jan
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