The purpose of this project was to synthesize two of the eight stereoisomers, SSR and SRS, of the natural product, Lentiginosine. Lentiginosine is a natural product and has been isolated from the plant <i>Astragalus lentiginosus</i>. The polyhydroxylated alkaloids extracted from this plant, swainsonine and lentiginosine, have been found to inhibit enzymes called glycosidases. These glycosidase enzymes are responsible for the processing of carbohydrates. Lentiginosine and its stereoisomers are members of a class of compounds called iminosugars. Iminosugars are sugar analogs with a nitrogen atom replacing the natural oxygen atom within the heterocyclic ring. As a result, iminosugars mimic the structure of sugars and bind to sugar processing enzymes such as glycosidases. If the iminosugars could be used to inhibit these enzymes, then the processing and degradation of sugars into their monomers would be prevented. These compounds are of interest in bioorganic and medicinal chemistry for the treatment of numerous diseases including cancer, Gaucher disease, viruses, and diabetes, among others.<br/>The goal is to synthesize all of the stereoisomers of lentiginosine, test their potency as inhibitors against glycosidases, and compare their potency to computer models of their binding in the active site of different glycosidases. Once their inhibitory properties are known, there is potential for pharmaceutical development. Therefore, in order to test these models, all eight stereoisomers of lentiginosine must be obtained for testing.

Synthesis of the SRS and SSR isomers of lentiginosine from D-glucopyranoside and D-galactopyranoside

249th National Meeting (2015)

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