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* Corresponding author 1 SEESIB - Synthèse et étude de systèmes à intêret biologique

Abstract : Versatile synthesis of some analogues of the naturally-occurring α-glucosidase inhibitor salacinol 1, involving thioanhydro alditol moieties with erythro, d,l-threo, xylo, ribo, d-arabino and d-manno configurations is described. Nucleophilic attack at the least-hindered carbon atom of an l- or d-protected erythritol cyclic sulfate by the thioanhydro alditol sulfur atom yielded the desired zwitterionic compounds. In addition, the preparation of the cyclic sulfates of 2,4-O-benzylidene-d-erythritol and 2,4-O-isopropylidene-l-erythritol was improved. Enzyme inhibition tests showed that most of the new compounds were weak but specific inhibitors, while good inhibitory activity was found for a six-membered ring analogue β-glucosidase: Ki=16 μM

keyword : Salacinol Glycosidase inhibitors Cyclic sulfate Thia-anhydroalditol Zwitterion Sulfonium sulfate inner salt





Autor: Estelle Gallienne - M. Benazza G. Demailly Jean Bolte - Marielle Lemaire -

Fuente: https://hal.archives-ouvertes.fr/



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