Stability of aminooxy glycosides to glycosidase catalysed hydrolysis

•Two beta-benzyl aminooxy glycosides have been synthesised.•These aminooxy glycosides are competitive glycosidase inhibitors.•Their O-benzyl glycoside analogues are shown to be substrates with the same enzymes.•This demonstrates the glycosidase stability of the aminooxy glycoside bond. The stability...

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Bibliographic Details
Published in:Carbohydrate research 2013-08, Vol.377, p.1-3
Main Authors: Iqbal, Amjid, Chibli, Hicham, Hamilton, Chris J.
Format: Article
Language:English
Subjects:
almonds
Aminooxy glycoside
beta-galactosidase
beta-Galactosidase - antagonists & inhibitors
beta-Galactosidase - chemistry
beta-glucosidase
beta-Glucosidase - antagonists & inhibitors
beta-Glucosidase - chemistry
Biocatalysis
Enzyme Assays
Enzyme Inhibitors - chemistry
Escherichia coli
Escherichia coli - chemistry
Escherichia coli - enzymology
Escherichia coli Proteins - antagonists & inhibitors
Escherichia coli Proteins - chemistry
galactose
glucose
Glycosidase
glycosides
Glycosides - chemistry
Hydrolysis
Inert substrate analogue
Kinetics
Plant Proteins - antagonists & inhibitors
Plant Proteins - chemistry
Prunus - chemistry
Prunus - enzymology
Solutions
Substrate Specificity
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Summary:•Two beta-benzyl aminooxy glycosides have been synthesised.•These aminooxy glycosides are competitive glycosidase inhibitors.•Their O-benzyl glycoside analogues are shown to be substrates with the same enzymes.•This demonstrates the glycosidase stability of the aminooxy glycoside bond. The stability of the amino(methoxy) beta-glycosidic bond to glycosidase catalysed hydrolysis is reported. Beta-O-benzyl glucose and beta-O-benzyl galactose are substrates hydrolysed by beta-glucosidase and beta-galactosidase from almonds and Escherichia coli, respectively. However their beta-N-benzyl-(O-methoxy)-glucoside and beta-N-benzyl-(O-methoxy)-galactoside derivatives are competitive inhibitors.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2013.05.006