Synthèse et étude de bêta-peptides glycoconjugués. Application en immunothérapie antitumorale

Abstract : β-peptides show a high stability towards proteolytic and metabolic processes. This work has been focused mainly on their use as multivalent platforms for the presentation of various carbohydrates, in particular tumor specific antigenic carbohydrate patterns, the socalled TACAs (Tumor-Associated Carbohydrate Antigen). TACAs, and among them the Tn antigen (GalNAc-α-O-Ser/Thr), are considered as cancer cells markers which can be integrated into fully synthetic structures aimed at mimicking tumor cells surface to induce an antitumoral immunologic response. In the first part of the thesis, the synthesis of β-peptides glycoconjugates, using the Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) has been investigated. These glycoconjugates containing up to six carbohydrate moities have been elaborated from azide- and alkyne-functionnalized β-peptides prepared from aspartic acid. The trimers of these glycoconjugated β-peptides were also coupled to biotine through an aminocaproic spacer and the constructs were tested for their antigenicity. Besides this, β- peptides exhibit a high tendancy to adopt secondary structures. That's why a conformational analysis of the β-peptide oligomers synthesized was carried out to determine the nature of a potential structuration.
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Theses
Organic chemistry. Université Blaise Pascal - Clermont-Ferrand II, 2009. French. <NNT : 2009CLF21998>


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Marielle Barra. Synthèse et étude de bêta-peptides glycoconjugués. Application en immunothérapie antitumorale. Organic chemistry. Université Blaise Pascal - Clermont-Ferrand II, 2009. French. <NNT : 2009CLF21998>. <tel-00724524>

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