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Bioscience, Biotechnology, and Biochemistry Volume 70, 2006 - Issue 10
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Original Articles

Chemoenzymatic Synthesis of a MUC1 Glycopeptide Carrying Non-Natural Sialyl TF-β O-Glycan

Eriko TANAKADepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
,
Yuko NAKAHARADepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
,
Yasuhiro KURODADepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
,
Yutaka TAKANODepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
,
Naoya KOJIMADepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
,
Hironobu HOJODepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
&
Yoshiaki NAKAHARADepartment of Applied Biochemistry, Institute of Glycotechnology, Tokai University
 show all
Pages 2515-2522 | Received 01 May 2006, Accepted 14 Jun 2006, Published online: 22 May 2014

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  • 2) Santos-Silva, F., Fonseca, A., Caffrey, T., Carvalho, F., Mesquita, P., Reis, C., Almeida, R., David, L., and Hollingsworth, M. A., Thomsen-Friedenreich antigen expression in gastric carcinomas is associated with MUC1 mucin VNTR polymorphism. Glycobiology, 15, 511–517 (2005).
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  • 5) Hanisch, F.-G., Stadie, T. R. E., Deutzmann, F., and Peter-Katalinic, J., MUC1 glycoforms in breast cancer. Cell line T47D as a model for carcinoma-associated alteration of O-glycosylation. Eur. J. Biochem., 236, 318–327 (1996).
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  • 9) Takano, Y., Habiro, M., Someya, M., Hojo, H., and Nakahara, Y., Preparation of core 2 type tetrasaccharide carrying decapeptide by benzyl protection-based solid-phase synthesis strategy. Tetrahedron Lett., 43, 8395–8399 (2002).
  • 10) Takano, Y., Kojima, N., Nakahara, Y., Hojo, H., and Nakahara, Y., Solid-phase synthesis of core 2 O-linked glycopeptide and its enzymatic sialylation. Tetrahedron, 59, 8415–8427 (2003).
  • 11) Takano, Y., Hojo, H., Kojima, N., and Nakahara, Y., Synthesis of a mimic for the heterogeneous surface of core 2 sialoglycan-linked glycoprotein. Org. Lett., 6, 3135–3138 (2004).
  • 12) Maemura, M., Ohgaki, A., Nakahara, Y., Hojo, H., and Nakahara, Y., Solid-phase synthesis of core 8 O-glycan-linked MUC5AC glycopeptide. Biosci. Biotechnol. Biochem., 69, 1575–1583 (2005).
  • 13) Hojo, H., Matsumoto, Y., Nakahara, Y., Ito, E., Suzuki, Y., Suzuki, M., Suzuki, A., and Nakahara, Y., 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 (2005).
  • 14) Takatani, M., Nakama, T., Manabe, S., Nakahara, Y., Ito, Y., and Nakahara, Y., Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage. Glycoconj. J., 17, 361–375 (2000).
  • 15) Nakahara, Y., Nonaka, T., Hojo, H., and Nakahara, Y., Synthesis of an unnatural N-glycan-linked dolichyl pyrophosphate precursor. Biosci. Biotechnol. Biochem., 67, 1761–1766 (2003).
  • 16) Bézay, N., Dudziak, G., Liese, A., and Kunz, H., Chemoenzymatic-chemical synthesis of a (2-3)-sialyl T threonine building block and its application to the synthesis of the N-terminal sequence of leukemia-associated leukosialin (CD 43). Angew. Chem. Int. Ed., 40, 2292–2295 (2001).
  • 17) Dziadek, S., and Kunz, H., Synthesis of a tumor-associated 2,3-sialyl-T glycododecapeptide antigen from the tamdem repeat region of the mucin MUC1. Synlett, 1623–1626 (2003).
  • 18) Hanisch, F.-G., Auerbach, B., Bosslet, K., Kolbe, K., Karsten, U., Nakahara, Y., Ogawa, Y., and Uhlenbruck, G., Monoclonal antibody BW494 defines a blood group Lewisa/Type 1 chain-related antigen on carcinoma-associated mucins. Biol. Chem. Hoppe-Seyler, 374, 1083–1091 (1993).
  • 19) Karsten, U., Serttas, N., Paulsen, H., Danielczyk, A., and Goltetz, S., Binding patterns of DTR-specific antibodies reveal a glycosylation-conditioned tumor-specific epitope of the epithelial mucin (MUC1). Glycobiology, 14, 681–692 (2004).
  • 20) Matsushita, T., Hinou, H., Kurogochi, M., Shimizu, H., and Nishimura, S., Rapid microwave-assisted solid-phase glycopeptide synthesis. Org. Lett., 7, 877–880 (2005).
  • 21) Fumoto, M., Hinou, H., Ohta, T., Ito, T., Yamada, K., Takimoto, A., Kondo, H., Shimizu, H., Inazu, T., Nakahara, Y., and Nishimura, S., Combinatorial synthesis of MUC1 glycopeptides: polymer blotting facilitates chemical and enzymatic synthesis of highly complicated mucin glycopeptides. J. Am. Chem. Soc., 127, 11804–11818 (2005).
  • 22) Nakahara, Y., Nakahara, Y., and Ogawa, T., Solid-phase synthesis of an O-linked glycopeptide based on a benzyl-protected glycan approach. Carbohydr. Res., 292, 71–81 (1996).
  • 23) Nakamura, K., Ishii, A., Ito, Y., and Nakahara, Y., A novel silyl linker: motif for side chain tethered approach to solid-phase glycopeptide synthesis. Tetrahedron, 55, 11253–11266 (1999).

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