Development of Methods for the Automated Synthesis of Plant and Microbial Oligosaccharides

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Through this award, funded by the Chemical Synthesis Program of the Division of Chemistry, Prof. Nicola Pohl from Indiana University-Bloomington and her students address two impediments to study of an important class of biomolecules called glycans, which are bioactive molecules containing linked chains of sugars. These stumbling blocks include both the lack of facile chemical methods to make well-defined sugar fragments and the availability of educational materials for introducing this class of biomolecules to budding chemists and biologists very early in their advanced education. The broader impacts of this proposed research include: 1) increasing participation of underrepresented groups by their inclusion in the proposed research and education activities; 2) advancing discovery and understanding through inclusion of graduate and undergraduate students as participants; 3) developing and disseminating educational materials that outline the role of carbohydrates beyond metabolism; and 4) developing robust automated methods to synthesize plant, viral and microbial oligosaccharides, a bottleneck to advancement of this line of research, since significant quantities of these materials are necessary for the study of their functions in a variety of biological, materials, and medical contexts.This project involves study and exploitation of the mechanism of a bismuth(V) complex discovered to promote glycosylation reactions using alkylthiol-linked sugars. The goal of the study is to better understand the chemistry that this relatively nontoxic element can effect and, in the process, to gain clues for how the glycosylation reaction can be accelerated. In addition, protocols to apply this new promoter to automated solution-phase oligosaccharide synthesis and to develop feasible building block strategies for the production of larger bioactive structures associated with important plant and microbial saccharides will be explored.