380 New Approaches to Expeditious Oligosaccharide Synthesis

Friday, November 6, 2009: 11:30 AM
Angus (Camino Real Hotel)
Sophon Kaeothip , Department of Chemistry and Biochemistry, University of Missouri - St. Louis, St. Louis, MO
Laurel K. Mydock , Department of Chemistry and Biochemistry, University of Missouri - St. Louis, St. Louis, MO
Hemali D. Premathilake , Department of Chemistry and Biochemistry, University of Missouri - St. Louis, St. Louis, MO
Alexei V. Demchenko , Department of Chemistry and Biochemistry, University of Missouri - St. Louis, St. Louis, MO
The involvement of complex carbohydrates in a wide variety of life-threatening cellular processes has given this class of natural compounds tremendous diagnostic and therapeutic potential.  While scientists have been able to successfully isolate certain classes of natural carbohydrates, the availability of pure natural isolates is still inadequate to address the challenges offered by modern glycosciences.  As a result, glycoscientists have turned to chemical synthesis as a means to access natural complex carbohydrates and their unnatural analogues.  Unfortunately, constructing oligosaccharides of even moderate complexity remains a considerable challenge, and more complex structures are not available at all.  As such, the development of efficient methods for the expeditious synthesis of complex carbohydrates stands out as a demanding area of research.
At the core of this presentation is the development of new methods, strategies, and technologies for expeditious oligosaccharide assembly.  New innovative tools for oligosaccharide synthesis such as thioimidate glycosylation approach, the temporary deactivation concept, the inverse armed-disarmed strategy, Surface-Tethered Iterative Carbohydrate Synthesis (STICS), etc. will be discussed.  The effectiveness of the methods developed will be illustrated by the synthesis of pneumococcal oligosaccharides (serotypes 6 and 14) as well as conjugates and mimetics thereof.
This work was generously supported by grants from AHA, NIAID, NIGMS, and NSF.