Introduction of Sharpless concept of click chemistry was also transplanted to carbohydrate chemistry 1-3. While, the original alkyne-azide concept of click-chemistry is well known, the alternative thiol-click is relatively unexplored. Our laboratory has developed one-pot, Thiol Enone Michael Addition (TEMA) click procedure protocol for the synthesis of new family of (1-5)-C-thiodisaccharides4. The feasibility of this new strategy has been demonstrated by the functionalization of new chiral epoxides nones 2  and 3  conveniently prepared in our laboratory from L- arabinose synthon 1.  Epoxides 2  & 3  undergoes base catalyzed Michael additions with D-galactose and glucose 1-thiols  via one step thiol-click approach. The exclusive regio- and stereochemistry of the Michael addition reaction proceeds with the formation of adducts 6-7  in high yields. The thio-click radical coupliung of ene 8   with 4'-thio-(1-5--thiodisaccharides 6-7  produces new tri-thiosaccharides 8-9  in excellent 92 % yield. They will be used as new tools for glycobiology and specifically as new inhibitors of galectin-3.5 The preliminary inhibition data of these thio-sugars will be discussed in details.  1. Click Chemistry in Glycoscience. New Developments and  Approaches. J. Wiley & Sons, NY, 2012. Z. J. Witczak, R. Bielski, Editors2. M. Fiore, A. Mara, and A. Dondoni, J. Org. Chem.,2009  , 74, 4422-4425.3. S. G. Gouin, L. Bultel, C. Falentin and J. Kovensky, Eur. J. Org. Chem. 2007 , 1160-1162.4. Z. J. Witczak, D. Lorchak and N. Nguyen, Carbohydr. Res., 2007 , 342, 1929-1931.5. Galectins, J. Wiley & Sons, NY, 2008. A. Klyosov, Z. J. Witczak, D. Platt, Editors

Thiol-enone Michael addition (TEMA) click approach to new selective inhibitors of galectin-3

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.