The involvement of complex carbohydrates in a wide variety of disease-related 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 glycoscience.  As a consequence, chemical synthesis has become a viable means to obtain both natural complex carbohydrates and unnatural analogues thereof.  Unfortunately, chemical synthesis of oligosaccharides of even moderate complexity still remains a considerable challenge, and many more complex structures are not available at all.  As such, the development of efficient methods for chemical glycosylation and expeditious oligosaccharide and glycoconjugates synthesis remains a demanding area of research.At the core of this presentation is the development of new methods, strategies, and technologies for chemical glycosylation and 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), thioimidate-only orthogonal and active-latent activation, and O-2/O-5 cooperative effect will be discussed in light of recent results.  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.

From chemical glycosylation to expeditious oligosaccharide synthesis

243rd National Meeting (2012)

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