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(Received for publication, August 21, 1996, and in revised form, September 16, 1996)
From the ¶ Department of Biochemistry, Duke University
Medical Center, Durham, North Carolina 27710 and the
Lipid A, the hydrophobic anchor of
lipopolysaccharides in the outer membranes of Gram-negative bacteria,
varies in structure among different Rhizobiaceae. The
Rhizobium meliloti lipid A backbone, like that of
Escherichia coli, is a
Volume 271, Number 50,
Issue of December 13, 1996
pp. 32126-32136
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.
and
Complex Carbohydrate Research Center, University of
Georgia, Athens, Georgia 30602
1
-6-linked glucosamine
disaccharide that is phosphorylated at positions 1 and 4.
Rhizobium leguminosarum lipid A lacks both phosphates, but
contains aminogluconate in place of the proximal glucosamine
1-phosphate, and galacturonic acid instead of the 4-phosphate. A
peculiar feature of the lipid As of all Rhizobiaceae is
acylation with 27-hydroxyoctacosanoic acid, a long hydroxylated fatty
acid not found in E. coli. We now describe an in
vitro system, consisting of a membrane enzyme and a cytosolic
acyl donor from R. leguminosarum, that transfers 27-hydroxyoctacosanoic acid to (Kdo)2-lipid
IVA, a key lipid A precursor common to both E. coli and R. leguminosarum. The 27-hydroxyoctacosanoic acid moiety was detected in the lipid product by mass spectrometry. The
membrane enzyme required the presence of Kdo residues in the acceptor
substrate for activity. The cytosolic acyl donor was purified from
wild-type R. leguminosarum using the acylation of (Kdo)2-[4-32P]-lipid IVA as the
assay. Amino-terminal sequencing of the purified acyl donor revealed an
exact 19-amino acid match with a partially sequenced gene
(orf*) of R. leguminosarum. Orf*
contains the consensus sequence, DSLD, for attachment of
4-phosphopantetheine. When the entire orf*
gene was sequenced, it was found to encode a protein of 92 amino acids.
Orf* is a new kind of acyl carrier protein because it is
only ~25% identical both to the constitutive acyl carrier protein
(AcpP) and to the inducible acyl carrier protein (NodF) of R. leguminosarum. Mass spectrometry of purified active
Orf* confirmed the presence of 4-phosphopantetheine and
27-hydroxyoctacosanoic acid in the major species. Smaller mass peaks
indicative of Orf* acylation with hydroxylated 20, 22, 24, and 26 carbon fatty acids were also observed. Given the specialized
function of Orf* in lipid A acylation, we suggest the new
designation AcpXL.
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