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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: plague [ICD11: 1B93

, ICD11: XN6QS

]; infection due to Yersinia pestis [ICD11: XN6QS

]

NCBI PubMed ID: 20454710
Journal NLM ID: 9610838
Publisher: Cambridge: Royal Society of Chemistry
Correspondence: peter.seeberger

mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14776 Potsdam, Germany, Freie Universita¨t Berlin Institut fu¨r Chemie und Biochemie, Arnimallee 22, 14195 Berlin, Germany

A short and enantioselective de novo synthesis of an L-glycero-D-manno-heptose building block for the total synthesis of a Yersinia pestis cell wall polysaccharide is described.

synthesis, cell wall polysaccharide, Yersinia pestis

Structure type: oligomer
Location inside paper: p.4106, fig.1
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_135813,IEDB_137340,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192

Methods: chemical synthesis
Synthetic data: chemical

NCBI Taxonomy refs (TaxIDs): 632
Show glycosyltransferases

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@H](O[C@@H]2[C@H](O)[C@@H](O[C@@H]3[C@H](O)[C@@H](O[C@@H]4[C@H](O[C@]5(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O5)C[C@](O)(C(=O)O)O[C@@H]4[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]3O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O[C@H]([C@@H](O)CO[C@H]3O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize