For many decades, carbohydrates (or sugars as they have been historically referred to), were considered to be far afield from mainstream organic chemistry. Already half a century ago, major advances were being made in physical organic chemistry, complex natural product synthesis,  establishment of rules of reactivity in bond formation, and important rearrangement reactions to mention a few. In the interim, carbohydrate chemists were preoccupied with identifying the nature of cell surface oligosaccharides, elucidating the structures of sugar components of antibiotics and their synthesis, different aspects of nucleoside chemistry, improvements in the synthesis of glycosides, and expanding the industrial applications  of polysaccharides such as starch, and cellulose. Carbohydrates occupy a special place among the subdisciplines of organic chemistry. Historically, Emil Fischer was able to correlate the absolute stereochemistry of D-alanine to that of D-glyceraldehyde. Carbohydrates have also been a fertile ground to validate the compatibility of new orthogonal protective groups and to test new bond forming reactions including classical examples of anchimeric assistance, and the study stereoelectronic effects.  Exploiting their inherent chirality, diversity of carbon framework, and conformational biases have made carbohydrates versatile building blocks (Chirons) in the total synthesis of complex natural products as well as drug molecules containing  one or more stereogenic centers. In recent years, the field of glycobiology has blossomed into an exciting area that combines advances in chemical proteomics with cellular events that involve exquisite recognition between carbohydrate residues and proteins of interest with far reaching implications in exploring the molecular basis of human disease. The lecture will feature selected vignettes highlighting “first to conceive and achieve” contributions in the field of carbohydrates spanning 50 years of active research in the Hanessian group at the University of Montreal.

Past and present carbohydrate chemistry vignettes from the Hanessian group

2019 Fall National Meeting

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