This project focuses on development of a fundamental understanding of the match between donor and acceptor reactants in carbohydrate chemistry, building from an empirical observation 30 years ago that some donors glycosidate a given acceptor-OH better than others. n-Pentenyl orthoesters (NPOEs) display exquisite regioselectivity as glycosyl donors, exceeding that of n-pentenyl glycosides. Through analysis of the early cationic intermediates of these donors, the origin of this selectivity enhancement will be deduced.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Bert O. Fraser-Reid, of the Natural Products and Glycotechnology Research Institute. Dr. Fraser-Reid is developing methods for the predictable, controlled synthesis of polysaccharides. These complex molecules, playing central roles in a wide variety of biological and biochemical processes, including cellular signaling and cell-cell recognition, are notoriously difficult to prepare synthetically. By focusing on an understanding of the factors influencing the reactivity of carbohydrates, Dr. Fraser-Reid is developing new and efficient synthetic methods, making these important molecules more accessible for study and ultimate development as, e.g., vaccines or diagnostic tools.
