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Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose
Authors:Jean-Bernard BehrCarine Chevrier,Albert Defoin,Cé  line TarnusJacques Streith
Affiliation:Laboratoire de Chimie Organique et Bioorganique, Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace.3, rue Alfred Werner, F-68093 Mulhouse Cédex, France
Abstract:Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-l-erythrose and 4-amino-5-deoxy-l-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose were potent β-d-glucosidase, α-d-mannosidase, α- and β-d-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of α-d-mannosidase.
Keywords:amino-sugars   aminoalditols   3,4-dihydroxypyrrolines   α-mannosidase inhibitor   glycosidase inhibitors
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