Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins
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Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins. / Bjerre, Jeannette; Nielsen, Erik Holm; Bols, Mikael.
In: European Journal of Organic Chemistry, 2008, p. 745-752.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins
AU - Bjerre, Jeannette
AU - Nielsen, Erik Holm
AU - Bols, Mikael
PY - 2008
Y1 - 2008
N2 - 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.
AB - 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.
KW - Faculty of Science
KW - Kunstigt Enzym
KW - Supramolekylær Kemi
KW - Glykosidase
KW - Artificial Enzyme
KW - Supramolecular Chemistry
KW - Glycosidase
U2 - 10.1002/ejoc.200700954
DO - 10.1002/ejoc.200700954
M3 - Journal article
SP - 745
EP - 752
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
ER -
ID: 1795623