βGal(1–3)GalNAc block donor for the synthesis of TF and α Sialy(2–6)TF as glycopeptide building blocks

作者: Dongxu Qiu , Sham S. Gandhi , R.Rao Koganty

DOI: 10.1016/0040-4039(95)02229-5

关键词:

摘要: Abstract 4,6-Benzylidene protected N-acetylgalactosamine β-glycosylated at the 3-position with peracetylated galactose is found to be an excellent donor for synthesis of Thomsen-Freidenreich (TF) family antigens. These may serve further as building blocks mucin derived glycopeptides and intermediates extention trisaccharides such sialyl-TF 6-O-βGlcNAc-TF(core 2). TF Sialylated are widely regarded tumor associated being investigated antigens immunotherapy cancers epithelial origin.

参考文章(10)
Howard J. Allen, Edward Clement Kisailus, Glycoconjugates : composition, structure, and function Dekker. ,(1992)
A Kurosaka, H Nakajima, I Funakoshi, M Matsuyama, T Nagayo, I Yamashina, Structures of the major oligosaccharides from a human rectal adenocarcinoma glycoprotein. Journal of Biological Chemistry. ,vol. 258, pp. 11594- 11598 ,(1983) , 10.1016/S0021-9258(17)44269-4
M. Madej, P. Y. S. Fung, B. M. Longenecker, R. R. Koganty, Active Specific Immunotherapy of a Murine Mammary Adenocarcinoma Using a Synthetic Tumor-associated Glycoconjugate Cancer Research. ,vol. 50, pp. 4308- 4314 ,(1990)
Yoshito Yamashita, Yong S. Chung, Ryuichi Horie, Reiji Kannagi, Michio Sowa, Alterations in Gastric Mucin With Malignant Transformation: Novel Pathway for Mucin Synthesis Journal of the National Cancer Institute. ,vol. 87, pp. 441- 446 ,(1995) , 10.1093/JNCI/87.6.441
Grant D. MacLean, Mark Reddish, R. Rao Koganty, Ting Wong, Sham Gandhi, Mark Smolenski, John Samuel, Jean Marc Nabholtz, B. Michael Longenecker, Immunization of breast cancer patients using a synthetic sialyl-Tn glycoconjugate plus Detox adjuvant. Cancer Immunology, Immunotherapy. ,vol. 36, pp. 215- 222 ,(1993) , 10.1007/BF01740902
G. D. MacLean, M. B. Bowen-Yacyshyn, J. Samuel, A. Meikle, G. Stuart, J. Nation, S. Poppema, M. Jerry, R. Koganty, T. Wong, B. M. Longenecker, Active immunization of human ovarian cancer patients against a common carcinoma (Thomsen-Friedenreich) determinant using a synthetic carbohydrate antigen. Journal of Immunotherapy. ,vol. 11, pp. 292- 305 ,(1992) , 10.1097/00002371-199205000-00008
R. Rao Koganty, Dongxu Qiu, Marc A. Riopel, Sham S. Gandhi, Ting C. Wong, John E. Yule, Steric control of N-acetylgalactosamine in glycosidic bond formation Tetrahedron Letters. ,vol. 36, pp. 6839- 6842 ,(1995) , 10.1016/0040-4039(95)01442-K
Hari G. Garg, Karsten von dem Bruch, Horst Kunz, Developments in the Synthesis of Glycopeptides Containing Glycosyl l-Asparagine, l-Serine, and l-Threonine Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 50, pp. 277- 310 ,(1994) , 10.1016/S0065-2318(08)60153-5