New methods and strategies for convergent oligosaccharide synthesis

CARB 12

Alexei V. Demchenko, demchenkoa@umsl.edu, Department of Chemistry & Biochemistry, University of Missouri - St. Louis, 434 Benton Hall (MC27), One University Boulevard, St. Louis, MO 63121-4499
The field of carbohydrate chemistry has experienced an explosive growth over the last two decades. This outbreak is mainly attributed to recent findings revealing the involvement of carbohydrates and their conjugates in a variety of biological processes including fundamental enzymatic and hormonal activities, interaction with invaders such as bacteria and viruses, connection with the development, growth, and metastasis of tumors, amongst others. The appreciation of the profound involvement of carbohydrates in a variety of processes in living organisms resulted in a strong demand for further investigation of these molecules. As a result of considerable difficulties associated with the isolation of pure natural glycostructures, the development of new stereoselective methods and convergent strategies for their chemical synthesis has come to the fore.

To enhance the ability to synthesize complex carbohydrates, our laboratory has been developing new methods and strategies for stereoselective glycosylation and convergent oligosaccharide synthesis. Amongst these, it has been established that S-benzoxazolyl and S-thiazolinyl glycosides are reactive and stereoselective glycosyl donors. Their ability to withstand many standard reaction conditions associated with protecting group manipulations and activation of other classes of glycosyl donors has led to a discovery of novel strategies for oligosaccharide assembly. These include the temporary deactivation concept, an unprecedented O-2/O-5 cooperative effect in glycosylation, and the inverse armed-disarmed strategy. In this new investigator award lecture, major accomplishments with the particular focus on recent developments will be overviewed.