ChemInform Abstract: Synthesis of Glycolipid Antigens

Carbohydrates and glycoconjugates play important roles in complex life processes. Development of carbohydrate-based therapeutics is a major focus of our laboratory requiring the synthesis of glycolipid antigens for biological evaluation. Stereoselective formation of O- and C-glycosides is one of the central challenges in carbohydrate synthesis. In this pursuit, we employ glycosyl iodides as unique glycosyl donors to construct functionally enriched appendages on the anomeric center of the sugar moiety in a highly efficient and stereoselective manner. These constructs can be used to rapidly synthesize a panoply of glycoside analogs for biological studies. In this minireview, glycosyl iodide mediated syntheses of α-linked O-glycolipids such as KRN 7000 and BbGL2 as well C-glycolipid analogs are described.