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JBC, Vol. 252, Issue 14, 4904-4912, Jul, 1977
P. D. Rick, L. W. Fung, C. Ho and M. J. Osborn
We describe here the isolation, purification, and structural
characterization of a lipid A precursor synthesized under nonpermissive
conditions by a mutant of Salmonella typhimurium conditionally defective in
the synthesis of the 3-deoxy-D-mannoctulosonate (2-keto-3-deoxyoctonate,
KDO) region of the lipopolysaccharide. The precursor was isolated free from
lipopolysaccharide, murein, and phospholipids by extraction of delipidated
cells with 90% phenol/CHCL3/petroleum ether. The molecule was recovered
from the phenol phase after precipitation of lipopolysaccharide with H2O
and subsequently purified by DEAE-cellulose chromatography. Structural
analyses showed that the lipid A precursor is a phosphorylated glucosamine
disaccharide containing one ester and two amide-linked residues of
beta-hydroxymyristate. In contrast to lipid A, the precursor disaccharide
lacks ester-linked 12:0 and 14:0 fatty acids as well as KDO. The molecule
contains 2 phosphate residues both of which were identified as
phosphomonoesters by 31P NMR spectroscopy. One of the phosphomonoesters is
located in position 1 of the reducing terminal glucosamine residue; the
location of the other phosphomonoester was not determined. The structure of
the precursor provides strong support for the conclusion that KDO
incorporation occurs at an early stage in lipid A biosynthesis prior to the
incorporation of ester-linked saturated fatty acids.
Lipid A mutants of Salmonella typhimurium. Purification and characterization of a lipid A precursor produced by a mutant in 3-deoxy-D-mannooctulosonate-8-phosphate synthetase
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