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Chlorination-elimination chemistry coupled with three-component Joullié-Ugi reaction and facile deprotection allowed efficient access to an array of polyhydroxylated pyrrolidines through parallel synthesis that may be considered to be a library of imino (aza) sugars (glycomimetics) and/or dihydroxyprolyl peptides (peptidomimetics). The utility of generating such a library was illustrated by screening against 15 different targets that revealed potent and selective inhibition of the Gaucher's disease glycosyltransferase enzyme glucosylceramide synthase and of primary pathogen model for human hepatitis C virus (HCV) and bovine diarrhoeal virus (BVDV). An observed selectivity for this HCV model over hepatitis B virus and remarkably low toxicity suggest a novel mode of action.

Original publication

DOI

10.1021/ja043924l

Type

Journal article

Journal

J Am Chem Soc

Publication Date

19/01/2005

Volume

127

Pages

506 - 507

Keywords

Antiviral Agents, Aza Compounds, Biomimetic Materials, Carbohydrates, Diarrhea Viruses, Bovine Viral, Enzyme Inhibitors, Erythritol, Glycopeptides, Glycoside Hydrolases, Hepatitis B virus, Hydroxyproline, Pyrrolidines, Sugar Alcohols