| HOME | HELP | FEEDBACK | SUBSCRIPTIONS | ARCHIVE | SEARCH | TABLE OF CONTENTS |
|
|
|
|||||||
|
|||||||||
J. Biol. Chem., Vol. 259, Issue 8, 4852-4859, Apr, 1984
BL Ray, G Painter and CR Raetz
We have discovered an enzyme in the cytosol of Escherichia coli that
generates lipid A disaccharides from monosaccharide precursors by the
following route: 2,3-diacyl-GlcN-1-P + UDP-2,3-diacyl-GlcN---- 2,3-
diacyl-GlcN (beta, 1----6) 2,3-diacyl-GlcN-1-P + UDP. Previous studies from
our laboratory have documented the presence in vivo of the precursors
2,3-diacylglucosamine 1-phosphate (2,3-diacyl-GlcN-1-P) (lipid X of E.
coli) and UDP-2,3-diacylglucosamine (UDP-2,3-diacyl- GlcN) (Bulawa, C.E.,
and Raetz, C.R.H.J. Biol. Chem. 259, 4846-4851). Both substrates are novel
glucosamine-derived phospholipids, acylated with beta-hydroxymyristoyl
moieties, and they accumulate in E. coli mutants defective in the pgsB
gene. Synthetic ADP-, GDP-, and CDP-2,3- diacylglucosamines are inefficient
substrates compared to the naturally occurring UDP derivative. The
free-acid form of the tetraacyldisaccharide 1-phosphate product
(C68H129N2O20P) that is generated in vitro has Mr = 1325.74 as judged by
fast atom bombardment mass spectrometry. Mild acid hydrolysis (0.1 M HCl
for 30 min at 100 degrees C) liberates greater than 95% of the phosphate
moiety as Pi. Detailed analysis by 1H and 13C NMR spectroscopy confirms the
presence of a phosphate residue at position 1 of the disaccharide, an
alpha- anomeric configuration at the reducing end, and a beta, 1----6
linkage between the two glucosamines. Importantly the disaccharide
1-phosphate synthase is missing in extracts of E. coli strains harboring
the pgsB1 mutation, consistent with the massive accumulation of
2,3-diacyl-GlcN-1- P and UDP-2,3-diacyl-GlcN in vivo. The enzymatic
reaction reported here represents a major biosynthetic route for the
formation of lipid A disaccharides in E. coli and other Gram-negative
bacteria. An in vitro system for the biosynthesis of lipid A disaccharides
has not been described previously.
The biosynthesis of gram-negative endotoxin. Formation of lipid A disaccharides from monosaccharide precursors in extracts of Escherichia coli
CiteULike 
Complore 
Connotea 
Del.icio.us 
Digg 
Reddit 
Technorati What's this?
This article has been cited by other articles:
|
|
 |
|
  C. M. Reynolds, S. R. Kalb, R. J. Cotter, and C. R. H. Raetz A Phosphoethanolamine Transferase Specific for the Outer 3-Deoxy-D-manno-octulosonic Acid Residue of Escherichia coli Lipopolysaccharide: IDENTIFICATION OF THE eptB GENE AND Ca2+ HYPERSENSITIVITY OF AN eptB DELETION MUTANT J. Biol. Chem., June 3, 2005; 280(22): 21202 - 21211. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 R. E. Bishop, E. I. Lo, M. Adil Khan, A. El Zoeiby, and W. Jia Enzymology of lipid A palmitoylation in bacterial outer membranes Innate Immunity, April 1, 2004; 10(2): 107 - 112. [Abstract] [PDF]
|
|
|
|
|
|
K. J. Babinski, A. A. Ribeiro, and C. R. H. Raetz The Escherichia coli Gene Encoding the UDP-2,3-diacylglucosamine Pyrophosphatase of Lipid A Biosynthesis J. Biol. Chem., July 12, 2002; 277(29): 25937 - 25946. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
K. J. Babinski, S. J. Kanjilal, and C. R. H. Raetz Accumulation of the Lipid A Precursor UDP-2,3-diacylglucosamine in an Escherichia coli Mutant Lacking the lpxH Gene J. Biol. Chem., July 12, 2002; 277(29): 25947 - 25956. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Z. Zhou, A. A. Ribeiro, and C. R. H. Raetz High-resolution NMR Spectroscopy of Lipid A Molecules Containing 4-Amino-4-deoxy-L-arabinose and Phosphoethanolamine Substituents. DIFFERENT ATTACHMENT SITES ON LIPID A MOLECULES FROM NH4VO3-TREATED ESCHERICHIA COLI VERSUS kdsA MUTANTS OF SALMONELLA TYPHIMURIUM J. Biol. Chem., April 28, 2000; 275(18): 13542 - 13551. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
T. J. O. Wyckoff and C. R. H. Raetz The Active Site of Escherichia coli UDP-N-acetylglucosamine Acyltransferase. CHEMICAL MODIFICATION AND SITE-DIRECTED MUTAGENESIS J. Biol. Chem., September 17, 1999; 274(38): 27047 - 27055. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
S. S. Basu, K. A. White, N. L. S. Que, and C. R. H. Raetz A Deacylase in Rhizobium leguminosarum Membranes That Cleaves the 3-O-Linked beta -Hydroxymyristoyl Moiety of Lipid A Precursors J. Biol. Chem., April 16, 1999; 274(16): 11150 - 11158. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
T. A. Garrett, N. L. S. Que, and C. R. H. Raetz Accumulation of a Lipid A Precursor Lacking the 4'-Phosphate following Inactivation of the Escherichia coli lpxK Gene J. Biol. Chem., May 15, 1998; 273(20): 12457 - 12465. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Z. Zhou, K. A. White, A. Polissi, C. Georgopoulos, and C. R. H. Raetz Function of Escherichia coli MsbA, an Essential ABC Family Transporter, in Lipid A and Phospholipid Biosynthesis J. Biol. Chem., May 15, 1998; 273(20): 12466 - 12475. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
T. A. Garrett, J. L. Kadrmas, and C. R. H. Raetz Identification of the Gene Encoding the Escherichia coli Lipid A 4'-Kinase. FACILE PHOSPHORYLATION OF ENDOTOXIN ANALOGS WITH RECOMBINANT LpxK J. Biol. Chem., August 29, 1997; 272(35): 21855 - 21864. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 W. Christ, O Asano, A. Robidoux, M Perez, Y Wang, G. Dubuc, W. Gavin, L. Hawkins, P. McGuinness, M. Mullarkey, et al. E5531, a pure endotoxin antagonist of high potency Science, April 7, 1995; 268(5207): 80 - 83. [Abstract] [PDF]
|
|
|
|
|
|
M. S. Trent, W. Pabich, C. R. H. Raetz, and S. I. Miller A PhoP/PhoQ-induced Lipase (PagL) That Catalyzes 3-O-Deacylation of Lipid A Precursors in Membranes of Salmonella typhimurium J. Biol. Chem., March 16, 2001; 276(12): 9083 - 9092. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
C. R. Sweet, S. Lin, R. J. Cotter, and C. R. H. Raetz A Chlamydia trachomatis UDP-N-Acetylglucosamine Acyltransferase Selective for Myristoyl-Acyl Carrier Protein. EXPRESSION IN ESCHERICHIA COLI AND FORMATION OF HYBRID LIPID A SPECIES J. Biol. Chem., May 25, 2001; 276(22): 19565 - 19574. [Abstract] [Full Text] [PDF]
|
|
| HOME | HELP | FEEDBACK | SUBSCRIPTIONS | ARCHIVE | SEARCH | TABLE OF CONTENTS |
| All ASBMB Journals | Molecular and Cellular Proteomics |
| Journal of Lipid Research | ASBMB Today |
