Taxonomic group: bacteria / Bacteroidetes, Proteobacteria
(Phylum: Bacteroidetes, Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 8112323Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Oral Microbiology, Osaka University, Faculty of Dentistry, Suita, Japan
Porphyromonas gingivalis 381 lipid A, characterized by β-(1-6)-linked glucosamine disaccharide 1-phosphate, with one hydroxyacyl group and one acyloxyacl group, i.e., 3-hydroxy-15-methyl-hexadecanoyl and 3-hexadecanoyloxy-15-methylhexadecanoyl groups at the 2 and 2' positions, respectively, was less endotoxically active than the synthetic Escherichia-coli-type lipid A (compound 506), which possesses β-(1-6)-linked glucosamine disaccharide 1,4'-bisphosphate, with two acyloxyacyl groups at the 2' and 3' positions and two 3-hydroxytetradecanoyl group at the 2 and 3 positions and the synthetic Salmonella-type lipid A (compound 516), which has three acyloxyacyl groups at the 2,2' and 3' positions and one hydroxyacyl group at the 3 position. P. gingivalis lipid A exhibited no or very low endotoxic activities, i.e., lethal toxicity in galactosamine-loaded mice, preparative ability for local Shwartzman reaction, pyrogenicity and Limulus test as compared with compounds 506 and 516. However, polyclonal B-cell activation of BALB/c mouse splenocytes was as strong as that of compound 506. Furthermore, P. gingivalis lipid A had stronger immunoadjuvant and hemagglutinating activities than compound 506. The absence of ester-linked phosphate at the 4' position and ester-linked fatty acids, and the presence and positions of fatty acids possessing considerable lengths of acyl chains are unique features of P. gingivalis lipid A, and they differentiate this lipid A from enterobacterial and other lipids A. The good balance between endotoxic properties and beneficial immunobiological activities of P. gingivalis lipid A may be attributable to these features.
Structure type: oligomer
Trivial name: lipid IVA
Compound class: LOS, lipid A, glycolipid
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864
Related record ID(s): 124179, 124444, 124446, 130438, 136955
NCBI Taxonomy refs (TaxIDs): 837,
562Reference(s) to other database(s): GlycomeDB:
7396
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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