ArticleThe Journal of organic chemistry2018
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.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 43 citations in OpenAlex.
- Current and emerging therapies for fungal biofilms and systemic infections.Critical reviews in microbiology · 2026Review
- Chemical Structure of a Branched α-d-Glucan from the Eggs of Sea UrchinInternational journal of molecular sciences · 2025Article
- Physico-chemical properties and substrate specificity of α-(1→3)-d-glucan degrading recombinant mutanase fromApplied and environmental microbiology · 2025Article
- Modeling of the Carbohydrate Oxacarbenium Ionic Intermediates of Glycosylation Reactions with Explicit Account for Protective Group Effects.ACS omega · 2025Article
- Application of the Chitooligosaccharides and Fluorescence Polarization Technique for the Assay of Active Lysozyme in Hen Egg White.Biomolecules · 2024Article
- Fluorescence Polarization Assay for Infection Diagnostics: A Review.Molecules (Basel, Switzerland) · 2024Review
- New synthesis of oligosaccharides modelling the M epitope of theFrontiers in chemistry · 2024Article
- Synthesis of branched and linear galactooligosaccharides related to glucuronoxylomannogalactan ofFrontiers in chemistry · 2024Article
- Identification of a new DC-SIGN binding pentamannoside epitope within the complex structure ofCell surface (Amsterdam, Netherlands) · 2023Article
- ASCA-related antibodies in the blood sera of healthy donors and patients with colorectal cancer: characterization with oligosaccharides related toFrontiers in molecular biosciences · 2023Article
- Synthesis of Fungal Cell Wall Oligosaccharides and Their Ability to Trigger Plant Immune Responses.European journal of organic chemistry · 2022Article
- Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection ofJournal of fungi (Basel, Switzerland) · 2021Article
- Glycoconjugate Vaccines for Prevention ofRussian journal of bioorganic chemistry · 2021Article
- Synthesis of biotinylated pentasaccharide structurally related to a fragment of glucomannan fromRussian chemical bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia · 2021Article
- Article
- Higher Cytokine and Opsonizing Antibody Production Induced by Bovine Serum Albumin (BSA)-Conjugated Tetrasaccharide Related toFrontiers in immunology · 2020Article
- Synthesis of Biotin-Tagged Chitosan Oligosaccharides and Assessment of Their Immunomodulatory Activity.Frontiers in chemistry · 2020Article
- Mannan detecting C-type lectin receptor probes recognise immune epitopes with diverse chemical, spatial and phylogenetic heterogeneity in fungal cell walls.PLoS pathogens · 2020Article
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- Importance ofFrontiers in cellular and infection microbiology · 2019Article
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Authors and funding
11 authors at 4 institutions in 3 countries.
Funding
Abstract
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.
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