Synthetic Oligosaccharides Mimicking Fungal Cell Wall Polysaccharides

Krylov, Vadim B.; Nifantiev, Nikolay E.

doi:10.1007/82_2019_187

Cited by 11 publications

(15 citation statements)

References 73 publications

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“…Biotinylated glycoconjugate ligands 1–18 ( Figure 2 ) [ 22 ] were chemically synthesized [ 23 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ] by means of coupling parent aminospacered oligosaccharides with an activated biotin derivative containing a hydrophilic hexaethylene glycol linker [ 42 ].…”

Section: Methodsmentioning

confidence: 99%

“…In a 1998 study that used oligomannosides prepared by depolymerization of the natural mannan, the minimal epitope of an anti- Candida albicans mannan monoclonal antibody EBCA-1 was claimed to be homo-α-(1→2)-mannopentaose [ 19 , 20 , 21 ]. Herein, we report the reinvestigation of the EBCA-1 carbohydrate specificity using the library of individual synthetic mannooligosaccharides related to the distinct fragments of the Candida mannan [ 22 ]. Modern methods of carbohydrate chemistry permit efficient and stereospecific assembling of complex oligosaccharide chains representing different parts of polysaccharides of the fungal cell wall [ 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

“…Herein, we report the reinvestigation of the EBCA-1 carbohydrate specificity using the library of individual synthetic mannooligosaccharides related to the distinct fragments of the Candida mannan [ 22 ]. Modern methods of carbohydrate chemistry permit efficient and stereospecific assembling of complex oligosaccharide chains representing different parts of polysaccharides of the fungal cell wall [ 22 , 23 , 24 ]. The arrays of oligosaccharides (glycoarrays) were shown to be indispensable tools in the assessment of ligand specificity of anti-carbohydrate monoclonal antibodies [ 25 , 26 , 27 , 28 , 29 , 30 , 31 ] and of antibodies in the blood sera [ 26 , 32 , 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

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Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection of Candida Mannan

Krylov

Solov’ev

Puchkin

et al. 2021

JoF

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Monoclonal antibody EBCA-1 is used in the sandwich immune assay for the detection of circulating Candida mannan in blood sera samples for the diagnosis of invasive candidiasis. To reinvestigate carbohydrate specificity of EBCA-1, a panel of biotinylated oligosaccharides structurally related to distinct fragments of Candida mannan were loaded onto a streptavidin-coated plate to form a glycoarray. Its use demonstrated that EBCA-1 recognizes the trisaccharide β-Man-(1→2)-α-Man-(1→2)-α-Man and not homo-α-(1→2)-linked pentamannoside, as was reported previously.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection of Candida Mannan

Krylov

Solov’ev

Puchkin

et al. 2021

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“…In particular, over the past few years, we have synthesized an array of biotinylated synthetic oligosaccharides representing fragments of fungal cell wall polysaccharides on streptavidincoated surfaces (Krylov and Nifantiev, 2020). Such arrays have been applied to assess carbohydrate specificity of monoclonal antibodies (Matveev et al, 2018(Matveev et al, , 2019Krylov et al, 2019;Schubert et al, 2019;Kazakova et al, 2020) and polyclonal antibodies in model sera induced by immunization of animals with cell wall preparations of various fungal species (Komarova et al, 2015;Paulovičová et al, 2016;Krylov et al, 2018a,b), as well as in sera obtained from patients with fungal infections (Komarova et al, 2018;Kazakova et al, 2020;Wong et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Biotin-Tagged Chitosan Oligosaccharides and Assessment of Their Immunomodulatory Activity

Tsvetkov

Paulovičová

et al. 2020

Front. Chem.

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Chitin, a polymer of β-(1→4)-linked N-acetyl-d-glucosamine, is one of the main polysaccharide components of the fungal cell wall. Its N-deacetylated form, chitosan, is enzymatically produced in the cell wall by chitin deacetylases. It exerts immunomodulative, anti-inflammatory, anti-cancer, anti-bacterial, and anti-fungal activities with various medical applications. To study the immunobiological properties of chitosan oligosaccharides, we synthesized a series of β-(1→4)-linked N-acetyl-d-glucosamine oligomers comprising 3, 5, and 7 monosaccharide units equipped with biotin tags. The key synthetic intermediate employed for oligosaccharide chain elongation, a disaccharide thioglycoside, was prepared by orthogonal glycosylation of a 4-OH thioglycoside acceptor with a glycosyl trichloroacetimidate bearing the temporary 4-O-tert-butyldimethylsilyl group. The use of silyl protection suppressed aglycon transfer and provided a high yield for the target disaccharide donor. Using synthesized chitosan oligomers, as well as previously obtained chitin counterparts, the immunobiological relationship between these synthetic oligosaccharides and RAW 264.7 cells was studied in vitro. Evaluation of cell proliferation, phagocytosis, respiratory burst, and Th1, Th2, Th17, and Treg polarized cytokine expression demonstrated effective immune responsiveness and immunomodulation in RAW 264.7 cells exposed to chitin- and chitosan-derived oligosaccharides. Macrophage reactivity was accompanied by significant inductive dose- and structure-dependent protective Th1 and Th17 polarization, which was greater with exposure to chitosan- rather than chitin-derived oligosaccharides. Moreover, no antiproliferative or cytotoxic effects were observed, even following prolonged 48 h exposure. The obtained results demonstrate the potent immunobiological activity of these synthetically prepared chito-oligosaccharides.

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“…The α-glucoside bond is present in various α-(1 → 2)-, , α-(1 → 3)-, , α-(1 → 4)-, , and α-(1 → 6)-glucans produced by fungi and bacteria. Of particular interest are α-(1 → 3)-glucans, which are widely represented in fungus Aspergillus fumigatus, responsible for a plethora of diseases in immunocompromised people, and whose role in interaction with host immunity has been actively studied. − …”

Section: Introductionmentioning

confidence: 99%

Combination of 3-O-Levulinoyl and 6-O-Trifluorobenzoyl Groups Ensures α-Selectivity in Glucosylations: Synthesis of the Oligosaccharides Related to Aspergillus fumigatus α-(1 → 3)-d-Glucan

Komarova,

Novikova,

Gerbst

et al. 2023

J. Org. Chem.

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Stereospecific α-glucosylation of primary and secondary OHgroup at carbohydrate acceptors is achieved using glucosyl N-phenyltrifluoroacetimidate (PTFAI) donor protected with an electron-withdrawing 2,4,5-trifluorobenzoyl (TFB) group at O-6 and the participating levulinoyl (Lev) group at O-3. New factors have been revealed that might explain αstereoselectivity in the case of TFB and pentafluorobenzoyl (PFB) groups at O-6. They are of conformational nature and confirmed by DFT calculations. The potential of this donor, as well as the orthogonality of TFB and Lev protecting groups, is showcased by the synthesis of α-(1 → 3)-linked pentaglucoside corresponding to Aspergillus fumigatus α-(1 → 3)-D-glucan and of its hexasaccharide derivative, bearing β-glucosamine residue at the non-reducing end.

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Synthetic Oligosaccharides Mimicking Fungal Cell Wall Polysaccharides

Cited by 11 publications

References 73 publications

Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection of Candida Mannan

Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection of Candida Mannan

Synthesis of Biotin-Tagged Chitosan Oligosaccharides and Assessment of Their Immunomodulatory Activity

Combination of 3-O-Levulinoyl and 6-O-Trifluorobenzoyl Groups Ensures α-Selectivity in Glucosylations: Synthesis of the Oligosaccharides Related to Aspergillus fumigatus α-(1 → 3)-d-Glucan

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