Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins

Abstract

Abstract The hydrolysis of toxic 7‐hydroxycoumarin glucosides and other aryl and alkyl glucosides, catalyzed by modified α‐ and β‐cyclodextrin dicyanohydrins, was investigated using different UV, redox, or HPAEC detection assays. The catalyzed reactions all followed Michaelis–Menten kinetics, and an impressive rate increase of up to 7569 ( k cat / k uncat ) was found for the hydroxycoumarin glucoside substrate 4‐MUGP. Good and moderate degrees of catalysis ( k cat / k uncat ) of up to 1259 were found for the natural glucosides phloridzin and skimmin. By using a newly developed catechol detection UV‐assay, a weak degree of catalysis was also found for the toxic hydroxycoumarin esculin. A novel synthesized diaminomethyl β‐cyclodextrin showed a weak catalysis of p ‐nitrophenyl β‐ D ‐glucopyranoside hydrolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)