Heck, Marie-Pierre Vincent, Stéphane P. Murray, Brion W. Bellamy, François Wong, Chi-Huey Mioskowski, Charles Cyclic Amidine Sugars as Transition-State Analogue Inhibitors of Glycosidases: Potent Competitive Inhibitors of Mannosidases A series of monocyclic glycoamidines bearing different exocyclic amine, alcohol, or alkyl functionalities and bicyclic amidines derived from d-glucose and d-mannose were synthesized and tested as inhibitors of various glycosidases. All the prepared compounds demonstrated good to excellent inhibition toward glycosidases. In particular, the biscationic d-mannoamidine <b>9b</b> bearing an exocyclic ethylamine moiety proved to be a selective competitive inhibitor of α- and β-mannosidases (<i>K</i><sub>i</sub> = 6 nM) making it the most potent inhibitor of these glycosidases reported to date. A favorable <i>B</i><sub>2,5</sub> boat conformation might explain the selectivity of mannosidase inhibition compared to other glycosidases. glycosidase;Cyclic Amidine Sugars;6 nM;K i;exocyclic amine;bicyclic amidines;mannosidase inhibition;alkyl functionalities;Inhibitor;monocyclic glycoamidines;exocyclic ethylamine moiety;inhibitor 2004-02-25
    https://acs.figshare.com/articles/journal_contribution/Cyclic_Amidine_Sugars_as_Transition_State_Analogue_Inhibitors_of_Glycosidases_Potent_Competitive_Inhibitors_of_Mannosidases/3348625
10.1021/ja037822r.s001