From the building blocks of nature to disease-battling pharmaceuticals, carbohydrates have had a profound impact on evolution, society, economy, and human health. Numerous applications of these essential biomolecules in many areas of science and technology exist, foremost of which can be found in the development of therapeutic agents and diagnostic platforms. Although carbohydrates are highly desirable to the biological and medical community, chemically these molecules are very challenging targets because of the need for chemical functionalization, protecting and leaving group manipulations, controlling anomeric stereoselectivity, etc. Advances in chemistry and biochemistry have certainly simplified the synthesis of carbohydrates. However, the development of practical and general methodsfor chemical glycosylation1and expeditious oligosaccharide synthesis2remain demanding areas of research.
Recently our group has expanded technologies available for the synthesis of oligosaccharides using polymer supports.The new experimental set-up is based on an unmodified HPLC, equipment that is readily available in practically any synthetic or analytical laboratory.3Solution-based reagents are delivered using a software-controlled solvent delivery system (multi-headed pump). The reaction progress and completion can be monitored in real time using a standard UV detector. All steps of oligosaccharide assembly including loading, glycosylation, deprotection, and cleavage can be performed using this experimental set-up. Herein, we present our recent results on expanding this promising technology. This work was generously supported by an award from the NIGMS.
(1) Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance; Demchenko, A. V., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
(2) Smoot, J. T.; Demchenko, A. V.Adv. Carbohydr. Chem. Biochem.2009,62, 161-250.
(3) Vijaya Ganesh, N.; Fujikawa, K.; Tan, Y. H.; Stine, K. J.; Demchenko, A. V.Org. Lett.2012,14, 3036-3039.
