Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins

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Jeannette Bjerre, Erik Holm Nielsen, Mikael Bols

The hydrolysis of toxic 7-hydroxycoumarin glucosides and other aryl and alkyl glucosides, catalyzed by modified a- and ß-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 (kcat/kuncat) was found for the hydroxycoumarin glucoside substrate 4-MUGP. Good and moderate degrees of catalysis (kcat/kuncat) 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 ß-cyclodextrin showed a weak catalysis of p-nitrophenyl ß-D-glucopyranoside hydrolysis.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Pages (from-to)745-752
Number of pages8
Publication statusPublished - 2008

ID: 1795623