Synthesis of a novel glycopeptide by polymeranalogous reaction of gelatin with mono-6-para-toluenesulfonyl-β-cyclodextrin and its supramolecular properties.

A synthetic model glycoprotein was successfully synthesized using gelatin and mono-6-para-toluenesulfonyl-β-cyclodextrin which were reacted under microwave conditions in basic media. The resulting glycoprotein is observed to form intermolecular inclusion complexes through complexation of the aromatic moieties along the polymer chain by the attached cyclodextrins. This phenomenon was analyzed and proven by 2D NMR spectroscopy (ROESY) and dynamic light scattering (DLS). Above the denaturation temperature, a strong increase of the hydrodynamic diameter was found due to enhanced supramolecular agglomeration. Such a novel glycoprotein with supramolecular self-recognition would be promising in biomedical applications serving as a drug-delivery basis polymer.