TY  - JOUR
A1  - Pavashe, Prashant
A1  - Elamparuthi, Elangovan
A1  - Hettrich, Cornelia
A1  - Moeller, Heiko M.
A1  - Linker, Torsten
T1  - Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A
JF  - The journal of organic chemistry
N2  - 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-thio saccharides. 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.
Y1  - 2016
U6  - https://doi.org/10.1021/acs.joc.6b00987
SN  - 0022-3263
VL  - 81
SP  - 8595
EP  - 8603
PB  - American Chemical Society
CY  - Washington
ER  -