CARB 31 |
| Sugar analogs carrying nitrogen at the position of the endocyclic oxygen atom, so-called ‘iminosugars', form one of the most interesting class of glycomimetics. Most iminosugar derivatives are however simple iminoalditols related to 1-deoxynojirimycin and do not carry a substituant at the ‘anomeric' position. Thus precious aglycone-specific information is lost when such iminosugars are used to mimick glycosides as glycosidase or glycosyltransferase inhibitors. We have designed efficient methodologies for the stereoselective synthesis of nojirimycin-C-glycosides carrying simple alkyl chains (e.g. compounds 1 and 2) or functionalized groups (e.g. compound 3 and 4). The synthesis of a diversity of imino-C-glycosyl compounds will be described and the biological activites of selected compounds as inhibitors of human &beta-glucocerebrosidase and of glucosylceramide synthase will be reported.
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Iminosugars: Therapeutic Potential
8:30 AM-12:10 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- 202A, Oral
Division of Carbohydrate Chemistry |
