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J. Biol. Chem., Vol. 260, Issue 29, 15536-15541, 12, 1985
MS Anderson, CE Bulawa and CR Raetz
The Gram-negative bacterium Escherichia coli has previously been shown to
utilize two unique glucosamine (GlcN)-derived phospholipids in the
biosynthesis of lipid A disaccharides (Bulawa, C.E., and Raetz, C. R.H.
(1984) J. Biol. Chem. 259, 4846-4851; Ray, B. L., Painter, G.L., and Raetz,
C.R.H. (1984) J. Biol. Chem. 259, 4852-4859. We now present evidence that
these compounds, UDP-2,3-diacyl-GlcN and 2,3-diacyl-GlcN- 1-phosphate
(2,3-diacyl-GlcN-1-P), are generated in extracts of E. coli by fatty
acylation of UDP-GlcNAc. The initial reaction is an O- acylation of the
glucosamine ring, presumably of the 3-OH group, with
(R)-beta-hydroxymyristate, followed by removal of the acetyl moiety, and
further fatty acylation of the N atom with (R)-beta- hydroxymyristate to
yield UDP-2,3-diacyl-GlcN. Hydrolysis of the pyrophosphate bridge in this
molecule gives 2,3-diacyl-GlcN-1-P + UMP. In vivo pulse labeling with 32Pi
supports this postulated pathway, since UDP-2,3-diacyl-GlcN is labeled
prior to 2,3-diacyl-GlcN-1-P. UDP- glucosamine is inactive as a substrate
in the initial acylation reaction. These acylations show an absolute
specificity for fatty acyl moieties activated with acyl carrier protein. No
reaction is detected with fatty acyl-CoA or free fatty acid. The fatty
acylation of sugar nucleotides has not been reported previously in E. coli
or any other organism.
The biosynthesis of gram-negative endotoxin. Formation of lipid A precursors from UDP-GlcNAc in extracts of Escherichia coli
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