Organic Synthesis and Characterization (NMR, mass spectrometry) of Beta-Glucosyl-Cholesterol for Parkinson's Disease research

Abstract

The aim of this research consists in the organic synthesis and characterization of a synthetic equivalent of β-glucosylcholesterol bearing a terminal alkyne functionality to ascertain, in collaboration with a research group of biologists from University of Padova, the possible involvement of this class of derivatives in the Parkinson’s disease’s aetiology. The target molecule, thanks to the presence of a reactive acetylenic moiety is suitable to further conjugation by “Click Chemistry” with azido functionalized solid supports or fluorophores. The synthetic approach consisted into overall 12 synthetic steps to produce the 3 synthetic synthons (glucosyl, cholesteryl and acetylenic units) requested for the preparation of the final molecule. The synthesis of the three synthons has been almost completed and largely optimized and each intermediate has been thoroughly characterized by NMR spectroscopy and high resolution mass spectrometry. In the near future the final target molecule will be obtained through final coupling methods.