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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 34667585
Publication DOI: 10.1039/d1sc03852d
Journal NLM ID: 101545951
Publisher: Cambridge, UK: Royal Society of Chemistry
Correspondence: tlowary

ualberta.ca
Institutions: Department of Chemistry, University of Alberta Edmonton AB T6G 2G2 Canada, Institute of Biological Chemistry, Academia Sinica Academia Road, Section 2, #128, Nangang Taipei 11529 Taiwan

The biosynthesis of lipopolysaccharide (LPS), a key immunomodulatory molecule produced by gram-negative bacteria, has been a topic of long-term interest. To date, the chemical probes used as tools to study LPS biosynthetic pathways have consisted primarily of small fragments of the larger structure (e.g., the O-chain repeating unit). While such compounds have helped to provide significant insight into many aspects of LPS assembly, understanding other aspects will require larger, more complex probes. For example, the molecular interactions between polymeric LPS biosynthetic intermediates and the proteins that transfer them across the inner and outer membrane remain largely unknown. We describe the synthesis of two lipid-linked polysaccharides, containing 11 and 27 monosaccharide residues, that are related to LPS O-chain biosynthesis in Escherichia coli O9a. This work has led not only to multi-milligram quantities of two biosynthetic probes, but also provided insights into challenges that must be overcome in the chemical synthesis of structurally-defined polysaccharides.

Lipopolysaccharide, synthesis, Escherichia coli O9a

Structure type: oligomer
Location inside paper: p. 12192, fig. 1C
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_136104,IEDB_137340,IEDB_140116,IEDB_141111,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_150077,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_241100,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical synthesis, MALDI-TOF MS, glycosylation
Synthetic data: chemoenzymatic

Related record ID(s): 10961
NCBI Taxonomy refs (TaxIDs): 1010797
Show glycosyltransferases

There is only one chemically distinct structure:

$CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC/C=C(\C)CC/C=C(\C)CCC=C(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H]5O)[C@@H]4O)[C@@H]3O)[C@@H]2O)[C@@H]1O$

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at aDManp: variable unit count (2-6) was assumed to be 2