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Synthèse de thiooligosaccharides, précurseurs d'analogues de facteurs de nodulation

Abstract : We prepared thionalogues precursors of chemichal messengers (nod factors) which interfere during the process of nodulation in the symbiotic association between some leguminous plants and bacteria of the rhizobium family, during this association, the plants could fix the atmospheric nhitrogen metabolized by the action of the bacteria. Those analogues should help in the understanding of the different processes that occur during the plant/bacteria symbiosis and the nod factors hydrolysis by enzymes named chitinases. We decided to prepar functionalised analogues for which only one o-glycosidic bond between two units would be replaced by a thioglycosidic bond. We used trichloroacetimidates as glycosil donors to synthesise a thiothrisaccharide and a thiotetrasaccharide (analogues precursor of nod factors) for which the reducing and the non reducing units are potentially differentiated in order to functionalise them. Moreover, a thiotrisaccharide was prepared by transferring a glucosamine unit on a thiodisaccharide unsing the β-1,4-galactosyltransferase. This last step allowed us to consider the synthesis of a thiotetresaccharide bu chemio-enzymatic way. Those precursors sgould lead to new thionalogues of nod factors on which biological assays could be made in order to evaluate the nodulation activity and the chitinases resistance.
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Submitted on : Tuesday, January 24, 2012 - 9:46:32 AM
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  • HAL Id : tel-00662408, version 1


Latino Loureiro Morais. Synthèse de thiooligosaccharides, précurseurs d'analogues de facteurs de nodulation. Chimie organique. Université Blaise Pascal - Clermont-Ferrand II, 2004. Français. ⟨NNT : 04CLF22493⟩. ⟨tel-00662408⟩



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