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  • Title: Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring.
    Author: Aguilar-Moncayo M, Gloster TM, Turkenburg JP, García-Moreno MI, Ortiz Mellet C, Davies GJ, García Fernández JM.
    Journal: Org Biomol Chem; 2009 Jul 07; 7(13):2738-47. PubMed ID: 19532990.
    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.
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