Towards the Synthesis of the Core Trisaccharide Region of Gangliosides
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Cell surface carbohydrates (e.g. gangliosides) are known to be involved in several important biological processes, including cell regulation , cellular interactions  and cell proliferation . Of particular interest to us are protein-carbohydrate interactions that are associated with the initial stages of bacterial and viral infection . In this regard, the ganglioside GM1 has been implicated in the initial stages of infection of human cells with rotavirus . We have recently reported the synthesis of novel lactose-based sialylmimetics as inhibitors of rotavirus . As part of our goal to develop inhibitors of rotavirus, we are also interested in gaining a better understanding of the nature of the interaction of carbohydrate-binding proteins with their natural substrates. Our continued interest in the synthesis of novel sialylmimetics as useful biological probes  prompted us to consider the synthesis of the trisaccharide-based GM1 mimetic. The presented work will focus on the preparation of a trisaccharide precursor to the sialylmimetic, describing the advantages (& shortcomings) of the overall strategy.  I. Gouni-Berthold, C. Seul, Y. Ko, J. Hescheler and A. Sachinidis, Hypertension, 38, 1030 (2001)  M. Hirai, H. Iwase, S. Arai, T. Takizawa and K. Hayashi, Biophys. J., 74, 1380 (1998).  F. Wang, N. E. Buckley, A. Olivera, K.A. Goodemote, Y. Su and S. Spiegel, Glycoconjugate J. 13, 937 (1996).  P. Isa, M. Realpe, P. Romero, S. L㰥z and C.F. Arias, Virology, 322, 370 (2004)  C.-T. Guo, O. Nakagomi, M. Mochizuki, H. Ishida, M. Kiso, Y. Ohta, T. Suzuki, D. Miyamoto, K.I.-P.J. Hidari and Y. Suzuki, J. Biochem., 126, 683 (1999)  A. Liakatos, M.J. Kiefel, F. Fleming, B. Coulson, and M. von Itzstein, Bio. Med. Chem, 14, 739 (2006)  M.J. Kiefel and M. von Itzstein, Chem. Rev., 102, 471 (2002)
Abstracts of the XXIII International Carbohydrate Symposium
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