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J Biol Chem, Vol. 274, Issue 26, 18503-18514, June 25, 1999
,
From the Two-thirds of the lipid A in wild-type
Escherichia coli K12 is a hexa-acylated disaccharide of
glucosamine in which monophosphate groups are attached at positions 1 and 4'. The remaining lipid A contains a monophosphate substituent at
position 4' and a pyrophosphate moiety at position 1. The biosynthesis
of the 1-pyrophosphate unit is unknown. Its presence is associated with
lipid A translocation to the outer membrane (Zhou, Z., White, K. A., Polissi, A., Georgopoulos, C., and Raetz, C. R. H. (1998)
J. Biol. Chem. 273, 12466-12475). To determine if a
phosphatase regulates the amount of the lipid A 1-pyrophosphate, we
grew cells in broth containing nonspecific phosphatase inhibitors.
Na2WO4 and sodium fluoride
increased the relative amount of the 1-pyrophosphate slightly.
Remarkably, NH4VO3-treated cells generated
almost no 1-pyrophosphate, but made six major new lipid A derivatives
(EV1 to EV6). Matrix-assisted laser desorption ionization/time of
flight mass spectrometry of purified EV1 to EV6 indicated that these
compounds were lipid A species substituted singly or in
combination with palmitoyl, phosphoethanolamine, and/or
aminodeoxypentose residues. The aminodeoxypentose residue was released
by incubation in chloroform/methanol (4:1, v/v) at 25 °C, and was
characterized by 1H NMR spectroscopy. The chemical shifts
and vicinal coupling constants of the two anomers of the
aminodeoxypentose released from EV3 closely resembled those of
synthetic 4-amino-4-deoxy-L-arabinose. NH4VO3-induced lipid A modification did not
require the PhoP/PhoQ two-component regulatory system, and also
occurred in E. coli msbB or htrB mutants. The
lipid A variants that accumulate in NH4VO3-treated E. coli K12 are the
same as many of those normally found in untreated Salmonella
typhimurium and Salmonella minnesota, demonstrating that E. coli K12 has latent enzyme systems
for synthesizing these important derivatives.
Department of Biochemistry, Duke University
Medical Center, Box 3711, Durham, North Carolina 27710 and the
§ Department of Pharmacology and Molecular Sciences, The
Johns Hopkins University School of Medicine,
Baltimore, Maryland 21205
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