Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37627
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Title: Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring
Authors: Aguilar Moncayo, Matilde, Gloster, Tracey M., Turkenburg, Johan P., García Moreno, María Isabel, Ortiz-Mellet, Carmen, Davies, Gideon J., García-Fernández, José Manuel
Keywords: Enzyme inhibitors
Indolizidines
Stereoisomerism
Thermodynamics
Thiourea
Castanospermine
Beta-Glucosidase
β-glucosidase
Issue Date: 22-May-2009
Publisher: Royal Society of Chemistry (Great Britain)
Abstract: Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of the appropriate beta-anomer by the beta-glucosidase.
Description: 10 páginas, 4 figuras, 3 tablas, 2 esquemas.
Publisher version (URL): http://dx.doi.org/10.1039/B906968B
URI: http://hdl.handle.net/10261/37627
ISSN: 1177-0520
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10.1039/B906968B
Citation: Organic and Biomolecular Chemistry 7(13): 2738-2747 (2009)
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