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J. Biol. Chem., Vol. 265, Issue 26, 15410-15417, Sep, 1990
KA Brozek and CR Raetz
In previous studies we described enzyme(s) from Escherichia coli that
transfer two 3-deoxy-D-manno-octulosonate (KDO) residues from two CMP- KDO
molecules to a tetraacyldisaccharide-1,4'-bis-phosphate precursor of lipid
A, termed lipid IVA (Brozek, K. A., Hosaka, K., Robertson, A. D., and
Raetz, C. R. H. (1989) J. Biol. Chem. 264, 6956-6966). The product,
designated (KDO)2-IVA, can be prepared in milligram quantities and/or
radiolabeled with 32P at position 4' of the IVA moiety. We now demonstrate
the presence of enzymes in E. coli extracts that transfer laurate and/or
myristate residues from lauroyl or myristoyl-acyl carrier protein (ACP) to
(KDO)2-IVA. Thioesters of coenzyme A are not substrates. The cytosolic
fraction catalyzes rapid acylation with lauroyl-ACP, but not with
myristoyl, R-3-hydroxymyristoyl, palmitoyl, or palmitoleoyl-ACP. The
membrane fraction transfers both laurate and myristate to (KDO)2-IVA.
Evidence for the enzymatic acylation of (KDO)2- IVA is provided by (a)
conversion of [4'-32P](KDO)2-IVA to more rapidly migrating products in the
presence of the appropriate acyl-ACP, (b) incorporation of [1-14C]laurate
or [1-14C]myristate into these metabolites in the presence of (KDO)2-IVA,
(c) fast atom bombardment- mass spectrometry, and (d) 1H NMR spectroscopy.
At protein concentrations less than 0.5 mg/ml, the acylation of (KDO)2-IVA
by the cytoplasmic fraction is absolutely dependent upon the addition of
exogenous acyl-ACP. These acyltransferases cannot utilize lipid IVA as a
substrate, demonstrating that they possess novel KDO recognition domains.
The unusual substrate specificity of these enzymes provides compelling
evidence for their involvement in lipid A biosynthesis. Depending on the
conditions it is possible to acylate (KDO)2-IVA with 1 or 2 lauroyl
residues, with 1 or 2 myristoyl residues, or with 1 of each.
Biosynthesis of lipid A in Escherichia coli. Acyl carrier protein- dependent incorporation of laurate and myristate
Department of Biochemistry, University of Wisconsin-Madison 53706.
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