Synthesis of a Pentasaccharide and Neoglycoconjugates Related to Fungal α-(1→3)-Glucan and Their Use in the Generation of Antibodies to Trace Aspergillus fumigatus Cell Wall - Archive ouverte HAL Access content directly
Journal Articles Chemistry - A European Journal Year : 2015

Synthesis of a Pentasaccharide and Neoglycoconjugates Related to Fungal α-(1→3)-Glucan and Their Use in the Generation of Antibodies to Trace Aspergillus fumigatus Cell Wall

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Abstract

3-Aminopropyl α-(1→3)-pentaglucoside, a fragment of α-(1→3)-glucan of the cell wall of Aspergillus fumigatus, has been synthesized in a blockwise approach. The application of mono- and disaccharide N-phenyltrifluoroacetimidates bearing a stereodirecting 6-O-benzoyl group was essential for stereoselective α-glucosylations. In the products, p-methoxyphenyl and levulinoyl groups served as orthogonal protecting groups for the anomeric position and 3-OH group, respectively. Their removal from shared blocks led to donors and acceptors that were used for the synthesis of pentasaccharides. Coupling of free α-(1→3)-pentaglucoside with biotin and bovine serum albumin (BSA) gave glycoconjugate tools for mycological studies. Immunization of mice with the BSA conjugate induced the generation of antibodies that recognize α-(1→3)-glucan on A. fumigatus cell wall and distinguish its morphotypes. This discovery represents a first step to the development of a diagnostic test system and a vaccine to detect and fight this life-threatening pathogen.

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pasteur-02515848 , version 1 (23-03-2020)

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Bozhena Komarova, Maria Orekhova, Yury Tsvetkov, Remi Beau, Vishukumar Aimanianda, et al.. Synthesis of a Pentasaccharide and Neoglycoconjugates Related to Fungal α-(1→3)-Glucan and Their Use in the Generation of Antibodies to Trace Aspergillus fumigatus Cell Wall. Chemistry - A European Journal, 2015, 21 (3), pp.1029-1035. ⟨10.1002/chem.201404770⟩. ⟨pasteur-02515848⟩

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