Synthesis of Glyco-Microspheres via a Thiol-Ene Coupling Reaction

A very simple pathway to generate microspheres via thiol-ene chemistry with sugar groups, which retain their biological activity, has been reported. The morphology and the surface of the microspheres were studied with optical microscope, scanning electron microscope (SEM) and Nuclear magnetic resonance (NMR). The coupling reaction is biologically friendly as it is compatible with water and oxygen and the process is simple, both advantages are quite attractive for synthesis of carbohydrate related materials. Thiol-ene chemistry was shown to be an efficient way to transform traditional or commercially available microspheres into highly bioactive particles. Vinyl functionalities, which we localized not only on the surface of the microsphere, but also at high concentrations in the interior of the sphere, reacted with glucothiose forming microspheres with a high bioactivity. These microspheres could selectively bind Con A, a reaction, which could be reversed in the presence of a strong competitive ligand such as mannose.