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J. Biol. Chem., Vol. 260, Issue 30, 16080-16088, Dec, 1985
CR Raetz, S Purcell, MV Meyer, N Qureshi and K Takayama
Temperature-sensitive mutants of Salmonella typhimurium that are defective
in the biosynthesis of 3-deoxy-D-manno-octulosonate are known to accumulate
disaccharide precursor(s) of lipid A at 42 degrees C (Rick, P. D., Fung, L.
W.-M., Ho, C., and Osborn, M. J. (1977) J. Biol. Chem. 252, 4904-4912). We
have devised new methods for purifying this material by chromatography on
DEAE-cellulose and silicic acid columns and have fractionated it into eight
related anionic components that fall into four sets, as judged by their
charge. Substances IA and IB have an apparent net charge of -1, IIA and IIB
of -2, IIIA and IIIB of - 3, and IVA and IVB of -4. Negative ion fast atom
bombardment mass spectrometry reveals that the simplest component is IVA [(
M - H]- at m/z 1404). Compound IVA is also the most abundant, representing
30-50% of the accumulated lipids after 3 h at 42 degrees C. Structural
studies of IVA, including NMR spectroscopy described in the accompanying
paper, reveal that it consists of
O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-(1- ---6)-2-amino-2-deoxy-alpha -
D-glucose, acylated at positions 2, 3, 2', and 3' with
beta-hydroxymyristoyl moieties and bearing phosphate groups at positions 1
and 4'. Compound IIIA ([M - H]- at m/z 1527) contains an additional
phosphoethanolamine residue, while IIA ([M - H]- m/z 1535) bears an
aminodeoxypentose substituent, presumably 4-amino-4- deoxy-L-arabinose.
Compound IA ([M - H]- at m/z 1658) bears both a phosphoethanolamine and an
aminodeoxypentose. The compounds of the less abundant B series are further
derivatized with an ester-linked palmitoyl moiety. Our results demonstrate
that these precursors are far more heterogeneous than previously suspected.
Isolation and characterization of eight lipid A precursors from a 3- deoxy-D-manno-octylosonic acid-deficient mutant of Salmonella typhimurium
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