Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Bacillus anthracis [ICD11:
XN94F 
]
Publication DOI: 10.1021/jacs.8b08857Journal NLM ID: 7503056Publisher: American Chemical Society
Correspondence: g.j.h.p.boons
uu.nl; gjboons
ccrc.uga.edu
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, GA, USA, United States, Department of Chemistry, University of Georgia, Athens, GA, USA, United States, Department of Chemical Biology and Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, and Bijvoet Center for Biomolecular Research, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands
The secondary cell wall polysaccharide (SCWP) of Bacillus anthracis plays a key role in the organization of the cell envelope of vegetative cells and is intimately involved in host-guest interactions. Genetic studies have indicated that it anchors S-layer and S-layer-associated proteins, which are involved in multiple vital biological functions, to the cell surface of B. anthracis. Phenotypic observations indicate that specific functional groups of the terminal unit of SCWP, including 4,6- O-pyruvyl ketal and acetyl esters, are important for binding of these proteins. These observations are based on genetic manipulations and have not been corroborated by direct binding studies. To address this issue, a synthetic strategy was developed that could provide a range of pyruvylated oligosaccharides derived from B. anthracis SCWP bearing base-labile acetyl esters and free amino groups. The resulting oligosaccharides were used in binding studies with a panel of S-layer and S-layer-associated proteins, which identified structural features of SCWP important for binding. A single pyruvylated ManNAc monosaccharide exhibited strong binding to all proteins, making it a promising structure for S-layer protein manipulation. The acetyl esters and free amine of SCWP did not significantly impact binding, and this observation is contrary to a proposed model in which SCWP acetylation is a prerequisite for association of some but not all S-layer and S-layer-associated proteins.
synthesis, Oligosaccharides, Synthetic, cell wall polysaccharide, Bacillus anthracis
Structure type: oligomer
Location inside paper: p.17080, fig.1
Aglycon: (1->4) cell wall polysaccharide
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_885813
Methods: NMR, ELISA, chemical synthesis, chemical methods, glycosylation, binding assays
Comments, role: terminal unit of secondary cell wall polysaccharide of B. anthracis
NCBI Taxonomy refs (TaxIDs): 1392
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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