Development of Diastereoselective C-linked Glycosides

Methodologies that have been reported by Crich and Kahne have demonstrated a means for the stereoselective synthesis of N-linked and O-linked glycosides from inexpensive and readily available starting materials.  We are anticipating that this methodology may be exploited to stereoselectively synthesize C-glycosides from a common sulfoxide precursor by varying the reaction conditions. The methodology developed will be tested for various common saccharides.

Once developed, the methodology will be applied to the synthesis of specific glycopeptides and glycolipids that have been targeted due to their over-expression on various types of cancer cell membranes.  The C-linked glycoconjugate derivatives will be tested for immune response; the ultimate objective being the development of effective carbohydrate based anti-tumor vaccines.