Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide

Milhomme, Ophélie; Köhler, Susanne M.; Ropartz, David; Lesur, David; Pilard, Serge; Djedaïni‐Pilard, Florence; Beyer, Wolfgang; Grandjean, Cyrille

doi:10.1039/c2ob26131f

Cited by 8 publications

(7 citation statements)

References 32 publications

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“…This study also showed that disaccharide neoglycoconjugates generated using thiol‐maleimide conjugation with a carbohydrate‐to‐protein ratio of 6 had similar antibody titres when compared to disaccharide neoglycoconjugate with a higher (19) carbohydrate‐to‐protein ratio …”

Section: Application and Impact Of Variables In Antibacterial Glycocsupporting

confidence: 52%

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An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity

Khatun

Stephenson

Tóth

2017

Chemistry A European J

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Bacterial cell-surface-derived or mimicked carbohydrate moieties that act as protective antigens are used in the development of antibacterial glycoconjugate vaccines. The carbohydrate antigen must have a minimum length or size to maintain the conformational structure of the antigenic epitope(s). The presence or absence of O-acetate, phosphate, glycerol phosphate and pyruvate ketal plays a vital role in defining the immunogenicity of the carbohydrate antigen. The nature of the carrier protein, spacer and conjugation pattern used to develop the glycoconjugate vaccine also defines its overall spatial orientation which in turn affects its avidity and selectivity of interaction with the desired target(s). In addition, the ratio of carbohydrate to protein in glycoconjugate vaccines also makes an important contribution in determining the optimum immunological response. This Review article presents the importance of these variables in the development of antibacterial glycoconjugate vaccines and their effects on immune efficacy.

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Section: Application and Impact Of Variables In Antibacterial Glycocsupporting

confidence: 52%

“…Milhomme et al. found that a disaccharide (Figure b) neoglycoconjugate consisting of 2‐hydroxy anthrose and rhamnose conjugated to the BSA carrier‐protein generated IgG antibodies that bound with the tetrasaccharides of native pathogen spores …”

Section: Application and Impact Of Variables In Antibacterial Glycocmentioning

confidence: 99%

An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity

Khatun

Stephenson

Tóth

2017

Chemistry A European J

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“…Recently, a 2-O-demethylated-b-D-anthropyranosyl-(1!3)-a-L-rhamnopyranose disaccharide analog of the tetrasaccharide unit was synthesized and conjugated to BSA [83]. An antinative tetrasaccharide IgG antibody response was achieved in BALB/c mice and induced sera were shown to bind to native endospores.…”

Section: Immune Response Against the Conjugated Tetrasaccharidementioning

confidence: 99%

Glycan surface antigens fromBacillus anthracisas vaccine targets: current status and future perspectives

Adamo

2014

Expert Review of Vaccines

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Over recent years great attention has been directed to the discovery of novel antigens from Bacillus anthracis, because of the potential of its spores in the development of weapons for mass destruction. Substantial effort has been directed to the identification and immunochemical evaluation of glycans that might be used for specific diagnostic detection of the spores or immune-mediated prevention of anthrax. Carbohydrate structures found on surfaces of vegetative cells and spores are herein discussed. Among them, the cell wall polysaccharide and the tetrasaccharide unit isolated from the exosporium protein BclA were proven immunogenic in an animal model after covalent linkage to carrier protein. Further investigation is needed to fully assess the potential of these promising carbohydrate antigens for vaccine development.

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“…Assays conducted on monoclonal antibodies that target B. anthracis glycan (38,43,44) have established the immunodominant character of anthrose (38,45,46) potentially specific for B. anthracis spores (47). Similarly, spore surface carbohydrates have showed the potential of eliciting the anti-spore IgG antibodies in mice, which opens the possibility of inserting carbohydrate haptens in vaccine formulations (48). However, despite these successes, the usage of anthrose-specific reagents for treatment and diagnostic purposes presents several limitations, including (a) the more widespread presence of anthrose in B. cereus and B. thuringiensis groups than initially expected (49,50), (b) the identification of B. anthracis strains devoid of anthrose (51), and (c) the presence of anthrose analogues in the capsular polysaccharide of a Shewanella sp.…”

Section: Discussionmentioning

confidence: 99%

Glycosylation of BclA Glycoprotein from Bacillus cereus and Bacillus anthracis Exosporium Is Domain-specific

Maës

Krzewinski

Garenáux

et al. 2016

Journal of Biological Chemistry

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The spores of the Bacillus cereus group (B. cereus, Bacillus anthracis, and Bacillus thuringiensis) are surrounded by a paracrystalline flexible yet resistant layer called exosporium that plays a major role in spore adhesion and virulence. The major constituent of its hairlike surface, the trimerized glycoprotein BclA, is attached to the basal layer through an N-terminal domain. It is then followed by a repetitive collagen-like neck bearing a globular head (C-terminal domain) that promotes glycoprotein trimerization. The collagen-like region of B. anthracis is known to be densely substituted by unusual O-glycans that may be used for developing species-specific diagnostics of B. anthracis spores and thus targeted therapeutic interventions. In the present study, we have explored the species and domain specificity of BclA glycosylation within the B. cereus group. First, we have established that the collagen-like regions of both B. anthracis and B. cereus are similarly substituted by short O-glycans that bear the species-specific deoxyhexose residues anthrose and the newly observed cereose, respectively. Second we have discovered that the C-terminal globular domains of BclA from both species are substituted by polysaccharide-like O-linked glycans whose structures are also species-specific. The presence of large carbohydrate polymers covering the surface of Bacillus spores may have a profound impact on the way that spores regulate their interactions with biotic and abiotic surfaces and represents potential new diagnostic targets.All Bacillus spores share a common architecture that consists of a set of concentric layers with a nucleotide-containing inner core surrounded by a peptidoglycan cortex and a spore coat. Species may differ according to the presence or not of an additional loosely fitting envelope enclosing individual spores. Indeed, mature spores from the Bacillus cereus group, which includes B. cereus, Bacillus anthracis, and Bacillus thuringiensis, are surrounded by a protein-rich, flexible envelope called the exosporium, whereas other species such as Bacillus subtilis and Bacillus licheniformis are not (1-3). Exosporia appear as a semipermeable barrier and are thought to exhibit a wide range of functions, including resistance to chemical and enzymatic treatments (4), enhancement of spore adhesion to biotic (5) and abiotic surfaces (6, 7), and germination (8). Some of the properties of the exosporium may also exert an influence on the infection process of pathogenic B. anthracis strains by protecting spores from macrophage-induced degradation (4, 9) and by targeting them toward phagocytic cells (5). As revealed by electron microscopy, the exosporium is made up of an external hairlike nap that sits on top of a paracrystalline basal layer (10, 11). The supporting basal layer of B. anthracis was shown to contain about 20 different proteins (12, 13) that form hexagonal subunits to which the hairlike structures are attached (11,14,15). Filaments are mostly composed of trimers of the major BclA glycoprotein (for ...

show abstract

Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide

Cited by 8 publications

References 32 publications

An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity

An Overview of Structural Features of Antibacterial Glycoconjugate Vaccines That Influence Their Immunogenicity

Glycan surface antigens fromBacillus anthracisas vaccine targets: current status and future perspectives

Glycosylation of BclA Glycoprotein from Bacillus cereus and Bacillus anthracis Exosporium Is Domain-specific

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