A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2004

A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction

Résumé

The reactions of 4-nitroaldehydes 9 and 10 with dihydroxyacetonephosphate (DHAP) catalyzed by fructose-1,6-diphosphate aldolase from rabbit muscle were studied. Starting from 9 or 10, only one main stereomer of nitrocyclitol 8 was isolated. A highly stereoselective intramolecular cyclization (Henry reaction or nitroaldol reaction) took place under acidic conditions during the aldolase catalyzed condensation and phytase catalyzed phosphate hydrolysis coupled step. The catalytic hydrogenation of nitrocyclitol 8 yielded aminocyclitol 7, a valiolamine analogue. Its inhibition properties were evaluated towards five glycosidases

Domaines

Chimie organique
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Dates et versions

hal-00135937 , version 1 (09-03-2007)

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Lahssen El Blidi, Dominique Crestia, Estelle Gallienne, Colette Demuynck, Jean Bolte, et al.. A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction. Tetrahedron: Asymmetry, 2004, 15, pp.2951-2954. ⟨10.1016/j.tetasy.2004.06.029⟩. ⟨hal-00135937⟩
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