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Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from d-galacturonic acid

Abstract : This paper describes a convenient and efficient synthesis of new complexing surfactants from d-galacturonic acid and n-octanol as renewable raw materials in a two-step sequence. In the first step, simultaneous O-glycosidation–esterification under Fischer conditions was achieved. The anomeric ratio of the products was studied based on the main experimental parameters and the activation mode (thermal or microwave). In the second step, aminolysis of the n-octyl ester was achieved with various functionalized primary amines under standard thermal or microwave activation. The physico-chemical properties of these new amphiphilic ligands were measured and these compounds were found to exhibit interesting surface properties. Complexing abilities of one uronamide ligand functionalized with a pyridine moiety toward Cu(II) ions was investigated in solution by EPR titrations. A solid compound was also synthesized and characterized, its relative structure was deduced from spectroscopic data.
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https://hal.univ-reims.fr/hal-02545906
Contributor : Laurent Dupont <>
Submitted on : Friday, April 17, 2020 - 3:03:34 PM
Last modification on : Wednesday, May 27, 2020 - 7:44:02 AM

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Anas Allam, Jean-Bernard Behr, Laurent Dupont, Véronique Nardello-Rataj, Richard Plantier-Royon. Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from d-galacturonic acid. Carbohydrate Research, Elsevier, 2010, 345 (6), pp.731-739. ⟨10.1016/j.carres.2010.01.009⟩. ⟨hal-02545906⟩

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