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Synthèse chimioenzymatique et évaluation d'inhibiteurs potentiels de glycosidases, analogues de la valiolamine

Abstract : Glycosidases are enzymes involved in many biological processes. In consequence, their inhibitors have many potential applications such as antidiabetic, antiviral drugs and are also used for treating genetic diseases. In the course of this work, we developed a chemoenzymatic process, to give access to analogues of valiolamine, a potent α-glucosidase inhibitor. Our aim was to prepare aminocyclitols bearing the amino group at a different position than the one found in valiolamine and with hydroxyl groups of various stereochemistries. Therefore we prepared the aminocyclitols using an original method based on an one-pot process involving two enzymes and three reactions : aldolization catalyzed by the fructose- 1,6-bisphosphate aldolase, dephosphorylation catalyzed by phytase and intramolecular nitroaldolization. Two C-C bonds were formed with a high stereoselectivity. In consequence, nine new aminocyclitols and two new zwitterions and one N-alkyl derivative were synthesized. Some aminocyclitols have shown a selectivity towards sweet almond β- glucosidase and Aspergillus oryzae β-galactosidase.
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Submitted on : Wednesday, June 13, 2012 - 11:18:06 AM
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  • HAL Id : tel-00707646, version 1

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Lahssen El Blidi. Synthèse chimioenzymatique et évaluation d'inhibiteurs potentiels de glycosidases, analogues de la valiolamine. Chimie analytique. Université Blaise Pascal - Clermont-Ferrand II, 2006. Français. ⟨NNT : 2006CLF21692⟩. ⟨tel-00707646⟩

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