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Chemical Synthesis and Application of Biotinylated Oligo-α-(1 → 3)-d-Glucosides To Study the Antibody and Cytokine Response against the Cell Wall α-(1 → 3)-d-Glucan of Aspergillus fumigatusстатья
Информация о цитировании статьи получена из
Scopus
Дата последнего поиска статьи во внешних источниках: 22 июня 2022 г.
- Авторы: Komarova Bozhena S., Wong Sarah S.W., Orekhova Maria V., Tsvetkov Yury E., Krylov Vadim B., Beauvais Anne, Bouchara Jean-Philippe, Kearney John F., Aimanianda Vishukumar, Latgé Jean-Paul, Nifantiev Nikolay E.
- Журнал: The journal of organic chemistry
- Том: 83
- Номер: 21
- Год издания: 2018
- Первая страница: 12965
- Последняя страница: 12976
- DOI: 10.1021/acs.joc.8b01142
- Аннотация: Biotinylated hepta-, nona- and undeca-α-(1 → 3)-d-glucosides representing long oligosaccharides of α-(1 → 3)-d-glucan, one of the major components of the cell walls of the fungal pathogen Aspergillus fumigatus, were synthesized for the first time via a blockwise strategy. Convergent assembly of the α-(1 → 3)-d-glucan chains was achieved by glycosylation with oligoglucoside derivatives bearing 6-O-benzoyl groups. Those groups are capable of remote α-stereocontrolling participation, making them efficient α-directing tools even in the case of large glycosyl donors. Synthetic biotinylated oligoglucosides (and biotinylated derivatives of previously synthesized tri- and penta-α-(1 → 3)-d-glucosides) loaded on streptavidin microtiter plates were shown to be better recognized by anti-α-(1 → 3)-glucan human polyclonal antibodies and to induce higher cytokine responses upon stimulation of human peripheral blood mononuclear cells than their natural counterpart, α-(1 → 3)-d-glucan, immobilized on a conventional microtiter plate. Attachment of the synthetic oligosaccharides equipped with a hydrophilic spacer via the streptavidin–biotin pair allows better spatial presentation and control of the loading compared to the random sorption of natural α-(1 → 3)-glucan. Increase of oligoglucoside length results in their better recognition and enhancement of cytokine production. Thus, using synthetic α-(1 → 3)-glucan oligosaccharides, we developed an assay for the host immune response that is more sensitive than the assay based on native α-(1 → 3)-glucan.
- Добавил в систему: Лопухов Антон Владимирович