Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 23413030Publication DOI: 10.1074/jbc.M113.453324Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: strent
mail.utexas.edu
Institutions: Department of Biochemistry, Duke University Medical Center, Durham, NC 27710, USA.
Lipopolysaccharide (LPS, endotoxin) is an essential component of the outer monolayer of nearly all Gram- negative bacteria. LPS is composed of a hydrophobic anchor, known as lipid A, an inner core oligosaccharide, and a repeating O-antigen polysaccharide. The first sugar bridging the hydrophopic lipid A and the polysaccharide domain is 3-deoxy-D-manno-octulosonic acid (Kdo) in nearly all species, and thus is critically important for LPS biosynthesis. Modifications to lipid A have been shown to be important for resistance to antimicrobial peptides as well as modulating recognition by the mammalian innate immune system. Therefore, lipid A derivatives have been used for development of vaccine strains and vaccine adjuvants. One derivative that has yet to be studied is 8-amino-3,8-dideoxy-D-manno-octulosonic acid (Kdo8N), which is found exclusively marine bacteria of the genus Shewanella. Using bioinformatics, a candidate gene cluster for Kdo8N biosynthesis was identified in Shewanella oneidensis. Expression of these genes recombinantly in E. coli resulted in lipid A containing Kdo8N, and in vitro assays confirmed their proposed enzymatic function. Both the in vivo and in vitro data were consistent with direct conversion of Kdo to Kdo8N prior to its incorporation into the Kdo8N-lipid A domain of LPS by a metal-dependent oxidase, followed by a glutamate-dependent aminotransferase. To our knowledge, this oxidase is the first enzyme shown to oxidize an alcohol using a metal and molecular oxygen, not NAD(P)+. Creation of an S. oneidensis in-frame deletion strain showed increased sensitivity to the cationic antimicrobial peptide polymyxin, as well as bile salts, suggesting a role in outer-membrane integrity.
Lipopolysaccharide, biosynthesis, lipid A, gene cluster, bioinformatics, Kdo8N, Shewanella oneidensis
Structure type: oligomer
Location inside paper: p.9219, fig.2A
Aglycon: lipid A
Trivial name: outer core region
Compound class: core oligosaccharide, LOS, LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659
Methods: SDS-PAGE, TLC, ESI-MS, genetic methods, biochemical methods, cloning
Biological activity: biochemical data
Biosynthesis and genetic data: genetic data
Related record ID(s): 29977
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G36348JQ, GlycomeDB:
5576
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There is only one chemically distinct structure:
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