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 |
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Authors: | Jean-Bernard BehrCarine Chevrier,Albert Defoin,Cé line TarnusJacques Streith |
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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 |
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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. |
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Keywords: | amino-sugars aminoalditols 3,4-dihydroxypyrrolines α-mannosidase inhibitor glycosidase inhibitors |
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