Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins

Jeannette Bjerre; Erik Holm Nielsen; Mikael Bols

doi:10.1002/ejoc.200700954

Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins

Jeannette Bjerre, Erik Holm Nielsen, Mikael Bols

Department of Chemistry

25 Citations (Scopus)

Abstract

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.

Translated title of the contribution	Hydrolyse af Naturligt Forekommende Toksiske Glukosider Katalyseret af Cyclodextrin Dicyanohydriner
Original language	English
Journal	European Journal of Organic Chemistry
Pages (from-to)	745-752
Number of pages	8
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.200700954
Publication status	Published - 2008

Keywords

Faculty of Science
Artificial Enzyme
Supramolecular Chemistry
Glycosidase

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@article{115afcf0a7e411dcbee902004c4f4f50,

title = "Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins",

abstract = "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.",

keywords = "Faculty of Science, Kunstigt Enzym, Supramolekyl{\ae}r Kemi, Glykosidase, Artificial Enzyme, Supramolecular Chemistry, Glycosidase",

author = "Jeannette Bjerre and Nielsen, {Erik Holm} and Mikael Bols",

year = "2008",

doi = "10.1002/ejoc.200700954",

language = "English",

pages = "745--752",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

}

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

SN - 1434-193X

SP - 745

EP - 752

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Hydrolysis of Toxic Natural Glucosides Catalyzed by Cyclodextrin Dicyanohydrins

Abstract

Keywords

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