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|Title:||New synthetic seven-membered 1-azasugars displaying potent inhibition towards glycosidases and glucosylceramide transferase|
Butters, Terry D.
Oikonomakos, Nikos G.
|Type:||Journal Article (Scientific Journal article)|
|Abstract:||Several members of a new family of seven-membered azasugars, which can be seen as 1-azasugar ring homologues, have been I obtained by simple chemical transformations starting from a sugar-derived azidolactol. Unlike their piperidine counterparts, these molecules are chemically stable when they possess a hydroxy group at the pseudo-C-2 position. Biological assays with a range of carbohydrate-processing enzymes have revealed interesting potential for these compounds. A trihydroxymethyl-substituted azepane displayed strong competitive inhibition on almond beta-glucosidase (K-i = 2.5 mu M) while a trihydroxylated corboxylic acid derivative proved to be a potent and selective L-fucosidase inhibitor K-i = 41 nM). N-Butylation of these seven-membered 1-azasugars generated derivatives with some activity towards the Gaucher's disease-related glucosylceramide transferase (IC50) 75 mu M) that did not interact significantly with digestive glucosidases.|
|Publisher:||Wiley-v C H Verlag Gmbh|
|Subject Category:||Science::Biology (General)|
Medicine::Pharmacy and materia medica
|Keywords:||azasugars; azepanes; Gaucher's disease; glycosidases; inhibitors; Chemistry, Medicinal|
|Other Identifiers:||DOI: http://dx.doi.org/10.1002/cbic.200700496|
|Rights holder:||© WILEY-V C H VERLAG GMBH|