Carbohydrates are one of the four main macromolecules consisting of carbon, hydrogen, and oxygen atoms joined together by glycosidic bonds. Glycosidic bonds between monomers of longer oligosaccharides are hydrolyzed by a class of enzymes known as glycoside hydrolases. The importance of this family of enzymes in carbohydrates processes can be used in the chemical development of treatments for cancer and diabetes. Through the general acid-base mechanism, the reducing enzyme mimics the oxo-carbenium like ion present in the transition state. The purpose of this research is to focus on the nitrogen-containing analogs of carbohydrates, specifically different stereoisomers of tetrahydroxylated iminosugars, to serve as a competitive inhibitor of these glycosidase enzymes. A key step in developing this pyrrolizidine involves a ruthenium dihydroxylation where the double bond in the alkene is converted into a diol. Synthetic methodology was used from commercially available D-glucose to investigate these iminosugars and develop a tetrahydroxylated pyrrolizidine.

Synthesis of tetrahydroxylated pyrrolizidine

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.