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 fumigatus

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 fumigatus Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2018, Volume: 83, Number: 21, Pages: 12965-12976 Pages count : 12 DOI: 10.1021/acs.joc.8b01142

Authors

Komarova Bozhena S. ¹ , Wong Sarah S.W. ² , Orekhova Maria V. ¹ , Tsvetkov Yury E. ¹ , Krylov Vadim B. ¹ , Beauvais Anne ² , Bouchara Jean-Philippe ³ , Kearney John F. ⁴ , Aimanianda Vishukumar ² , Latgé Jean-Paul ² , Nifantiev Nikolay E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia
2	Unité des Aspergillus, Institut Pasteur, 25 rue du Docteur Roux, 75724 Paris Cedex 15, France
3	Groupe d’Etude des Interactions Hôte-Pathogène (EA 3142), UNIV Brest, 74521-49045 Angers, France
4	University of Alabama, Birmingham, Alabama 35294-2182, United States

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.

Komarova B.S. , Wong S.S.W. , Orekhova M.V. , Tsvetkov Y.E. , Krylov V.B. , Beauvais A. , Bouchara J-P. , Kearney J.F. , Aimanianda V. , Latgé J-P. , Nifantiev N.E.
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 fumigatus
Journal of Organic Chemistry. 2018. V.83. N21. P.12965-12976. DOI: 10.1021/acs.joc.8b01142 WOS Scopus OpenAlex

≡ Web of science:	WOS:000449443200002
≡ Scopus:	2-s2.0-85055130242
≡ OpenAlex:	W2895621460