Glycomimetics are carbohydrate analogs with altered physical, physiological and/or biological properties based on structural changes compared to the respective parent compounds. Iminosugars are glycomimetics with the ring oxygen being replaced by a basic trivalent nitrogen, which are very well known for their manifold applications as tools and therapeutics based on their interactions with glycoside processing enzymes. Representatives of this compound class find application in the elucidation of enzyme mechanisms and disease pathways. For therapeutic purposes they are employed, for example, for the treatment of diabetes Type 2 (Miglitol®) and Gaucher disease Type 1 (Miglustat®). Other representatives have immunoregulating properties and anti-bacterial properties. Furthermore, some are considered to have potential for therapeutic disease management of Alzheimer’s as well as Parkinson disease. Recently, glycomimetics have been introduced as probes for activity based protein profiling (ABPP) of glycoprocessing enzymes. Employing these small molecules, ABPP allows for evaluation of protein function on a global cellular level by rapid, sensitive, and selective detection and verification of protein activity rather than abundance.
Our approach towards the design and syntheses of iminosugar based glycomimetics as potential therapeutics as well as probes for activity based protein profiling of glycoprocessing enzymes will be presented.
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