Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
Publication DOI: 10.1134/S1068162006050128Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: Vorobeva EV <tikhonovaev
mail.ru>
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok, Russia
The hydrolysis of defatted cells of the marine bacterium Chryseobacterium scophtalmum CIP 104199T with 10% acetic acid (3 h, 100°C) led to an unusual lipid A (LA) (yield 0.6%), obtained for the first time. Using chemical analysis, FAB MS, and NMR spectroscopy, it was shown to be D-glucosamine 1-phosphate acylated with (R)-3-hydroxy-15-methylhexadecanoic and (R)-3-hydroxy-13-methyltetroadecanoic acids at the C2 and C3 atoms, respectively. It is similar to the monosaccharide biosynthetic precursor of lipopolysaccharide (LPS), so-called lipid X (LX). Unlike LX, LA can be isolated by the treatment of bacteria with organic solvents only after the preliminary acidic hydrolysis of the cells, which suggests that LA might be strongly, probably chemically, linked to other components of the outer membrane. However, LPS cannot be such a component, because extraction with phenol-water or phenol-chloroform-petroleum ether mixtures in high yields (5.34% and 0.5%, respectively) leads to preparations that do not contain 3-deoxy-D-manno-oct-2- ulopyranosonic acid, 3-hydroxyalkanoic acids, or LA.
Lipopolysaccharide, lipid A, Chryseobacterium scophtalmum, lipid X
Structure type: monomer
Location inside paper: Fig.3, b, lipid X
Compound class: glycolipid
Contained glycoepitopes: IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, FAB-MS, SDS-PAGE, TLC, MALDI-TOF MS, NMR-1D, GPC, alkaline hydrolysis, extraction, optical rotation measurement
Related record ID(s): 43946
NCBI Taxonomy refs (TaxIDs): 83333
Show glycosyltransferases
There is only one chemically distinct structure:
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