Abstract
The O-glycoprotein is typically found in mucins, which are characterized by their heavily glycosylated tandem repeat regions. As an example of O-glycoprotein synthesis, the preparation of the repeating sequence of mucin by the ligation method is briefly descried. Fmoc-Ser/Thr units carrying glycan chains are prepared and used for the solid-phase synthesis of glycosylated peptide thioester, a key intermediate for glycoprotein synthesis. The peptide thioester is then repeatedly condensed to give a model of the repeating region of mucin.
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References
Gaidzik N, Westerlind U, Kunz H (2013) The development of synthetic antitumour vaccines from mucin glycopeptide antigen. Chem Soc Rev 42:4421–4442
Hojo H, Matsumoto Y, Nakahara Y, Ito E, Suzuki Y, Suzuki M, Suzuki A, Nakahara Y (2005) Chemical synthesis of 23 kDa glycoprotein by repetitive segment condensation: a synthesis of MUC2 basal motif carrying multiple O-GalNAc moieties. J Am Chem Soc 127:13720–13725
Iijima H, Nakahara Y, Ogawa T (1992) Synthesis of the N-terminal glycopentapeptides of human glycophorin AM and AN carrying trimeric sialosyl Tn epitope. Tetrahedron Lett 33:7907–7910
Ozawa C, Katayama H, Hojo H, Nakahara Y, Nakahara Y (2008) Efficient sequential segment coupling using N-alkylcysteine-assisted thioesterification for glycopeptide dendrimer synthesis. Org Lett 10:3531–3533
Ueki A, Takano Y, Kobayashi A, Nakahara Y, Hojo H, Nakahara Y (2009) Solid-phase synthesis of glycopeptide carrying a tetra-N-acetyllactosamine- containing core 2 decasaccharide. Tetrahedron 66:1742–1759
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Hojo, H. (2015). Synthesis of O-Glycoprotein. In: Taniguchi, N., Endo, T., Hart, G., Seeberger, P., Wong, CH. (eds) Glycoscience: Biology and Medicine. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54841-6_45
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DOI: https://doi.org/10.1007/978-4-431-54841-6_45
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Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-54840-9
Online ISBN: 978-4-431-54841-6
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