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Media type:
E-Article
Title:
Synthesis of glycosylated β3-homo-threonine conjugates for mucin-like glycopeptide antigen analogues
Contributor:
Karch, Florian;
Hoffmann-Röder, Anja
Published:
Beilstein Institut, 2010
Published in:
Beilstein Journal of Organic Chemistry, 6 (2010)
Language:
English
DOI:
10.3762/bjoc.6.47
ISSN:
1860-5397
Origination:
Footnote:
Description:
Glycopeptides from the mucin family decorated with tumour-associated carbohydrate antigens (TACA) have proven to be important target structures for the development of molecularly defined anti-cancer vaccines. The strategic incorporation of β-amino acid building blocks into such mucin-type sequences offers the potential to create pseudo-glycopeptide antigens with improved bioavailability for tumour immunotherapy. Towards this end, TN and TF antigen conjugates O-glycosidically linked to Fmoc-β3-homo-threonine were prepared in good yield via Arndt–Eistert homologation of the corresponding glycosyl α-amino acid derivative. By incorporation of TN-Fmoc-β3hThr conjugate into the 20 amino acid tandem repeat sequence of MUC1 using sequential solid-phase glycopeptide synthesis, a first example of a mixed α/β-hybrid glycopeptide building block was obtained. The latter is of interest for the development of novel glycoconjugate mimics and model structures for anti-cancer vaccines with increased biological half-life.