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Synthèse d’outils pour le marquage métabolique des glycanes.

Abstract : Glycans are biomolecules made up of a chain of monosaccharides bound together by glycosidic bonds. The nature and abundance ofmonosaccharides forming the glycanic chain and the arrangement of glycosylation patterns differ greatly depending on the organism of origin. The biosynthesis and degradation of these polysaccharide architectures are finely regulated by specific enzymatic systems and are organized within the various cell compartments. Glycans are used in various biological processes: energy reserves, protein folding and stability, cell recognition and adhesion to the extracellular matrix.This thesis focuses on the synthesis and use of compounds allowing the metabolic labeling of glycans of eukaryotic cells (cell line of prostate cancer, PC-3) or of diderm bacteria with mycomembranes (Corynebacterium glutamicum).The compounds synthesized or used in this thesis are saccharides functionalized by a bio-orthogonal groups (azido, alkyne or methylcyclopropene groups) or labeling tools simultaneously carrying a bio-orthogonal complementary function (cyclooctyne or tetrazine groups) and a label that can be detected by a macromolecule functionalized by fluorophores (D-biotin/streptavidine or 2,4-DiNitroPhenol/ anti-DNP antibodies). The solubility of labeling tools in aqueous media is a limiting factor. Part of the work of this thesis has been to develop more water-soluble labeling tools by adding a -sulfo--alanine pattern. This pattern has a sulfonic acid function, which is deprotonated at physiological pH, thus promoting aqueous solubility.The metabolic uptake of functionalized saccharides and the ability of tools to label cells (after metabolic uptake) are evaluated in either biological model, by flow cytometry analysis or confocal microscopy.
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Mathieu Carlier. Synthèse d’outils pour le marquage métabolique des glycanes.. Chimie organique. Université Paris-Saclay, 2019. Français. ⟨NNT : 2019SACLS453⟩. ⟨tel-02724768⟩

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