P. Pavashe, E. Elamparuthi, C. Hettrich, H. M. Möller, T. Linker
Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A
J. Org. Chem. 2016, 81, 8595
DOI: 10.1021/acs.joc.6b00987
A convenient and general synthesis of 2-thiocarbohydrates via cerium ammonium nitrate oxidation of the thiocyanate ion is described. Radical addition to glycals proceeds with excellent regio- and good stereoselectivities in only one step, deprotection affords water-soluble 2-thiosaccharides. Binding studies to Con A have been performed by isothermal titration calorimetry (ITC) and saturation transfer difference (STD) NMR spectroscopy. The 2-thiomannose derivative binds even stronger to Con A than the natural substrate, offering opportunities for new lectin or enzyme inhibitors.
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