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J Biol Chem, Vol. 274, Issue 16, 11150-11158, April 16, 1999
-Hydroxymyristoyl Moiety of Lipid
A Precursors
From the Department of Biochemistry, Duke University Medical
Center, Durham, North Carolina 27710
Lipid A from the nitrogen-fixing bacterium
Rhizobium leguminosarum displays many structural
differences compared with lipid A of Escherichia coli. R. leguminosarum lipid A lacks the usual 1- and 4'-phosphate groups
but is derivatized with a galacturonic acid substituent at position 4'.
R. leguminosarum lipid A often contains an aminogluconic
acid moiety in place of the proximal glucosamine 1-phosphate unit.
Striking differences also exist in the secondary acyl chains attached
to E. coli versus R. leguminosarum lipid A, specifically the presence of 27-hydroxyoctacosanoate and the
absence of laurate and myristate in R. leguminosarum. Recently, we have found that lipid A isolated by pH 4.5 hydrolysis of
R. leguminosarum cells is more heterogeneous than
previously reported (Que, N. L. S., Basu, S. S., White,
K. A., and Raetz, C. R. H. (1998) FASEB J. 12, A1284 (abstr.)). Lipid A species lacking the 3-O-linked
-hydroxymyristoyl residue on the proximal unit contribute to this
heterogeneity. We now describe a membrane-bound deacylase from R. leguminosarum that removes a single ester-linked -hydroxymyristoyl moiety from some lipid A precursors, including lipid X, lipid IVA, and
(3-deoxy-D-manno-octulosonic
acid)2-lipid IVA. The enzyme does not cleave
E. coli lipid A or lipid A precursors containing an
acyloxyacyl moiety on the distal glucosamine unit. The enzyme is not
present in extracts of E. coli or Rhizobium meliloti, but it is readily demonstrable in membranes of
Pseudomonas aeruginosa, which also contains a significant
proportion of 3-O-deacylated lipid A species. Optimal
reaction rates are seen between pH 5.5 and 6.5. The enzyme requires a
nonionic detergent and divalent metal ions for activity. It cleaves the
monosaccharide lipid X at about 5% the rate of lipid IVA
and (3-deoxy-D-manno-octulosonic acid)2-lipid IVA. 1H NMR
spectroscopy of the deacylase reaction product, generated with lipid
IVA as the substrate, confirms unequivocally that the enzyme cleaves only the ester-linked -hydroxymyristoyl residue at
the 3-position of the glucosamine disaccharide.
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