Solubility of N, N'-Disuccinimidyl Carbonate and its relevance to polysaccharide functionalization.

N, N'-Disuccinimidyl Carbonate (DSC) is a common reagent for the functionalization of polysaccharides for affinity chromatography. Difficulty in the removal of excess DSC after the functionalization reaction promoted the studies of its solubilities in organic solvents. Surprisingly, DSC has low solubility in several common organic solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and isopropanol. It is slightly soluble in acetone and acetonitrile, soluble in dimethylformamide, and very soluble in dimethyl sulfoxide. Solvent effect on DSC's use in the functionalization of the Sepharose-6-fastflow resin from GE Healthcare was also studied. While dimethyl sulfoxide did not improve the functionalization reaction, it proved to be an effective solvent removing excess DSC after the functionalization reaction.