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Acylation des flavonoïdes par les lipases de Candida antarctica et Pseudomonas cepacia : études cinétique, structurale et conformationnelle

Abstract : This work aims to study the performances and the regioselcetivity of two lipases throughout the acylation of flavonoids in organic medium. This study showed that the solubility in acetonitrile, acetone and tert-amyl alcohol depends on the nature of the flavonoid. The highest solubility, in actonitrile, was obtained with the naringenin and hesperitin and the lowest with rutin and isoquercitrin. The thermophysical properties are also affected by the nature of flavonoids. Thus glycosylated flavonoids are characterized by a low melting point and a high enthalpy of fusion compared to the aglycon ones. From the kinetic acylation data, the highest conversion yields of 99% were obtained with quercetin. These conversion yields vary according to the nature of the flavonoid and the acyl donor, the molar ratio (vinyl acetate/flavonoid) and the nature of the solvent. The lowest conversion yield was obtained with hesperitin. Molecular modeling of flavonoids in vacuum and solvents allows to study the role of conformation structure on solubility and to release the structure-activity relationship with many electronic descriptors. Finally, OPLS all atoms were built to study, by molecular dynamics, quercetin in condensed phases of organic solvents.
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Latifa Chebil. Acylation des flavonoïdes par les lipases de Candida antarctica et Pseudomonas cepacia : études cinétique, structurale et conformationnelle. Alimentation et Nutrition. Institut National Polytechnique de Lorraine, 2006. Français. ⟨NNT : 2006INPL097N⟩. ⟨tel-01752787⟩

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