Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 37
  Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" - Carbohydrate Research 338(23) (2003) 2431-2447
  

  Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.

  Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains

  NCBI PubMed ID: 14670707
  Publication DOI: 10.1016/j.carres.2003.07.010
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: martine.carloff@bbmpc.u-psud.fr
  Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
  
   
  
  Rhizobium etli
  CSDB ID 31472 (all data & tools)
• Article ID: 1438
  Basu SS, Karbarz MJ, Raetz CR "Expression cloning and characterization of the C28 acyltransferase of lipid A biosynthesis in Rhizobium leguminosarum" - Journal of Biological Chemistry 277(32) (2002) 28959-28971
  

  An unusual feature of lipid A from plant endosymbionts of the Rhizobiaceae family is the presence of a 27-hydroxyoctacosanoic acid (C28) moiety. An enzyme that incorporates this acyl chain is present in extracts of Rhizobium leguminosarum, Rhizobium etli, and Sinorhizobium meliloti but not Escherichia coli. The enzyme transfers 27- hydroxyoctacosanate from a specialized acyl carrier protein (AcpXL) to the precursor Kdo2 ((3-deoxy-d-manno-octulosonic acid)2)-lipid IV(A). We now report the identification of five hybrid cosmids that direct the overexpression of this activity by screening approximately 4000 lysates of individual colonies of an R. leguminosarum 3841 genomic DNA library in the host strain S. meliloti 1021. In these heterologous constructs, both the C28 acyltransferase and C28-AcpXL are overproduced. Sequencing of a 9-kb insert from cosmid pSSB-1, which is also present in the other cosmids, shows that acpXL and the lipid A acyltransferase gene (lpxXL) are close to each other but not contiguous. Nine other open reading frames around lpxXL were also sequenced. Four of them encode orthologues of fatty acid and/or polyketide biosynthetic enzymes. AcpXL purified from S. meliloti expressing pSSB-1 is fully acylated, mainly with 27-hydroxyoctacosanoate. Expression of lpxXL in E. coli behind a T7 promoter results in overproduction in vitro of the expected R. leguminosarum acyltransferase, which is C28-AcpXL-dependent and utilizes (3-deoxy-d-manno-octulosonic acid)2-lipid IV(A) as the acceptor. These findings confirm that lpxXL is the structural gene for the C28 acyltransferase. LpxXL is distantly related to the lauroyltransferase (LpxL) of E. coli lipid A biosynthesis, but highly significant LpxXL orthologues are present in Agrobacterium tumefaciens, Brucella melitensis, and all sequenced strains of Rhizobium, consistent with the occurrence of long secondary acyl chains in the lipid A molecules of these organisms

  biosynthesis, structure, cloning, lipid A, sequencing, Rhizobium leguminosarum, acyltransferase

  NCBI PubMed ID: 12019272
  Publication DOI: 10.1074/jbc.M204525200
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: raetz@biochem.duke.edu
  Institutions: Department of Biochemistry, Duke University Medical Center, Durham, North Carolina 27710, USA
  Methods: SDS-PAGE, DNA techniques, acid hydrolysis, genetic methods, biochemical methods, HPLC, enzyme assay, FPLC, bioinformatic analysis
  
   
  
  Rhizobium etli CE3
  CSDB ID 31643 (all data & tools)
• Article ID: 1477
  Que NLS, Ribeiro AA, Raetz CRH "Two-dimensional NMR spectroscopy and structures of six lipid species from Rhizobium etli. Detection of an acyloxyacyl residue in each component and origin of the aminogluconate moiety" - Journal of Biological Chemistry 275(36) (2001) 28017-28027
  

  The chemical structures of six lipid A species (A, B, C, D-1, D-2, and E) purified from Rhizobium etli CE3 were investigated by one- and two-dimensional NMR spectroscopy. The R. etli lipid A subtypes each contain an unusual acyloxyacyl residue at position 2' as part of a conserved distal glucosamine moiety but differ in their proximal units. All R. etli lipid A species lack phosphate groups. However, they are derivatized with an α-linked galacturonic acid group at position 4', as shown by nuclear Overhauser effect spectroscopy. Component B, which had been not been reported in previous studies, features a β1'-6 linked disaccharide of glucosamine acylated at positions 2, 3, 2', and 3' in a pattern that is typical of lipid A found in other Gram-negative bacteria. D-1 contains an acylated aminogluconate unit in place of the proximal glucosamine residue of B. C and E lack ester-linked beta-hydroxyacyl chains at position 3, as judged by their H-3 chemical shifts, and may be synthesized from B and D-1, respectively, by the R. etli 3-O-deacylase. D-2 is an isomer of D-1 that forms nonenzymatically by acyl chain migration. A may be an elimination product derived from D-1 during hydrolysis at 100 degrees C (pH 4.5), a step needed to release lipid A from lipopolysaccharide. Based on these findings, we propose a biosynthetic scheme for R. etli lipid A in which B is generated first by a variation of the E. coli pathway. The aminogluconate unit of D-1 could then be made from B by enzymatic oxidation of the proximal glucosamine. As predicted by our hypothesis, enzyme(s) can be demonstrated in extracts of R. etli that convert (14)C-labeled B to D-1.

  NMR, structure, Bacterial, lipid A, NMR spectroscopy, Rhizobium, Rhizobium etli, spectroscopy, two-dimensional, acyloxyacyl

  NCBI PubMed ID: 10856304
  Publication DOI: 10.1074/jbc.M004009200
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: raetz@biochem.duke.edu
  Institutions: Department of Biochemistry and the Duke NMR Spectroscopy Center and Department of Radiology, Duke University Medical Center, Durham, North Carolina 27710, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, TLC, MALDI-TOF MS, NMR-1D, DEAE, methylation analysis
  
   
  
  Rhizobium etli CE3, Rhizobium leguminosarum 3855
  CSDB ID 32043 (all data & tools)
• Article ID: 4621
  Sohlenkamp C, Raetz CR, Ingram BO "The calcium-stimulated lipid A 3-O deacylase from Rhizobium etli is not essential for plant nodulation" - Biochimica et Biophysica Acta 1831(7) (2013) 1250-1259
  

  The lipid A component of lipopolysaccharide from the nitrogen-fixing plant endosymbiont, Rhizobium etli, is structurally very different from that found in most enteric bacteria. The lipid A from free-living R. etli is structurally heterogeneous and exists as a mixture of species which are either pentaacylated or tetraacylated. In contrast, the lipid A from R. etli bacteroids is reported to consist exclusively of tetraacylated lipid A species. The tetraacylated lipid A species in both cases lack a β-hydroxymyristoyl chain at the 3-position of lipid A. Here, we show that the lipid A modification enzyme responsible for 3-O deacylation in R. etli is a homolog of the PagL protein originally described in Salmonella enterica sv. typhimurium. In contrast to the PagL proteins described from other species, R. etli PagL displays a calcium dependency. To determine the importance of the lipid A modification catalyzed by PagL, we isolated and characterized a R. etli mutant deficient in the pagL gene. Mass spectrometric analysis confirmed that the mutant strain was exclusively tetraacylated and radiochemical analysis revealed that 3-O deacylase activity was absent in membranes prepared from the mutant. The R. etli mutant was not impaired in its ability to form nitrogen-fixing nodules on Phaseolus vulgaris but it displayed slower nodulation kinetics relative to the wild-type strain. The lipid A modification catalyzed by R. etli PagL, therefore, is not required for nodulation but may play other roles such as protecting bacterial endosymbionts from plant immune responses during infection.

  Lipopolysaccharide, lipid A, Rhizobium etli, Gram-negative bacteria, pagL

  NCBI PubMed ID: 24046865
  Publication DOI: 10.1016/j.bbalip.2013.04.002
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Correspondence: chsohlen@ccg.unam.mx; B.O. Ingram
  Institutions: Department of Biochemistry, Duke University Medical Center, Durham, NC 27710, USA, Centro de Ciencias Genómicas, Universidad Nacional Autónoma de México, Av. Universidad s/n, Apdo. Postal 565-A, Cuernavaca, Morelos, CP62210, Mexico
  Methods: DNA techniques, TLC, ESI-MS, biological assays, genetic methods, biochemical methods, LC-MS, assay of polymyxin sensitivity, radiochemical analysis
  
   
  
  Rhizobium etli
  CSDB ID 32041 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772

• Article ID: 37
  Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" - Carbohydrate Research 338(23) (2003) 2431-2447
  

  Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.

  Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains

  NCBI PubMed ID: 14670707
  Publication DOI: 10.1016/j.carres.2003.07.010
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: martine.carloff@bbmpc.u-psud.fr
  Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
  
   
  
  Burkholderia caryophylli
  CSDB ID 31474 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_534865

• Article ID: 37
  Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" - Carbohydrate Research 338(23) (2003) 2431-2447
  

  Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.

  Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains

  NCBI PubMed ID: 14670707
  Publication DOI: 10.1016/j.carres.2003.07.010
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: martine.carloff@bbmpc.u-psud.fr
  Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
  
   
  
  Aquifex pyrophilus
  CSDB ID 31477 (all data & tools)
• Article ID: 6385
  Fux AC, Casonato Melo C, Michelini S, Swartzwelter BJ, Italiani P, Himly M "Heterogeneity of Lipopolysaccharide as Source of Variability in Bioassays and LPS-Binding Proteins as Remedy" - International Journal of Molecular Sciences 24(9) (2023) 8395
  

  Lipopolysaccharide (LPS), also referred to as endotoxin, is the major component of Gram-negative bacteria's outer cell wall. It is one of the main types of pathogen-associated molecular patterns (PAMPs) that are known to elicit severe immune reactions in the event of a pathogen trespassing the epithelial barrier and reaching the bloodstream. Associated symptoms include fever and septic shock, which in severe cases, might even lead to death. Thus, the detection of LPS in medical devices and injectable pharmaceuticals is of utmost importance. However, the term LPS does not describe one single molecule but a diverse class of molecules sharing one common feature: their characteristic chemical structure. Each bacterial species has its own pool of LPS molecules varying in their chemical composition and enabling the aggregation into different supramolecular structures upon release from the bacterial cell wall. As this heterogeneity has consequences for bioassays, we aim to examine the great variability of LPS molecules and their potential to form various supramolecular structures. Furthermore, we describe current LPS quantification methods and the LPS-dependent inflammatory pathway and show how LPS heterogeneity can affect them. With the intent of overcoming these challenges and moving towards a universal approach for targeting LPS, we review current studies concerning LPS-specific binders. Finally, we give perspectives for LPS research and the use of LPS-binding molecules.

  Lipopolysaccharide, lipid A, immunology, endotoxin, detection, low endotoxin recovery, LPS-binding molecules

  NCBI PubMed ID: 37176105
  Publication DOI: 10.3390/ijms24098395
  Journal NLM ID: 101092791
  Publisher: Basel, Switzerland: MDPI
  Correspondence: M. Himly
  Institutions: Division of Allergy & Immunology, Department of Biosciences & Medical Biology, Paris Lodron University of Salzburg (PLUS), Hellbrunnerstra?e 34, 5020 Salzburg, Austria, Chemical Biology Department, R&D Reagents, Miltenyi Biotec B.V. & Co. KG, Friedrich-Ebert-Straße 68, 51429 Bergisch Gladbach, Germany, Biotechnical Faculty, Department of Biology, University of Ljubljana, Večna pot 111, 1000 Ljubljana, Slovenia, Department of Microbiology, Immunology, and Pathology, 1601 Campus Delivery, Colorado State University, Fort Collins, CO 80523, USA, Experimental Medical Physics, Heinrich-Heine University Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany, Institute of Biochemistry and Cell Biology, Consiglio Nazionale delle Ricerche (CNR), Via P. Castellino 111, 80131 Naples, Italy, Stazione Zoologica Anton Dohrn (SZN), Villa Comunale, 80121 Naples, Italy
  
   
  
  Aquifex pyrophilus
  CSDB ID 22387 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531

• Article ID: 43
  Demchenko AV, Santhanam B, Moore JN, Boons G "Synthesis and biological evaluation of Rhizobium sin-1 lipid A derivatives" - Journal of the American Chemical Society 125(20) (2003) 6103-6112
  

  A highly convergent strategy for the synthesis of several derivatives of the lipid A of Rhizobium sin-1 has been developed. The approach employed the advanced intermediate 3-O-acetyl-6-O-(3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyrano-syl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (5), which is protected in such a way that the anomeric center, the C-2 and C-2' amino groups, and the C-3 and C-3' hydroxyls can be selectively functionalized. The synthetic strategy was used for the preparation of 2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxy-hexadecanoyl]-2-[(R)-3-octacosanoyloxy-hexadecan]amido-β-D-glucopyranosyl]-2-[(R)-3-hydroxy-hexadecan]amido-3-O-[(R)-3-hydroxy-hexadecanoyl]-α-D-glucopyranose (11) and 2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxy-hexadecanoyl]-2-[(R)-3-octacosanoyloxy-hexadecan]amido-β-D-glucopyranosyl]-2-[(R)-3-hydroxy-hexadecan]amido-3-O-[(R)-3-hydroxy-hexadecanoyl]-d-glucono-1,5-lactone (13), which contain an unusual octacosanoic acid moiety and differ in the oxidation state of the anomeric center. The results of biological studies indicate that 11 and 13 lack the proinflammatory effects of Escherichia coli lipopolysaccharides (LPS). Furthermore, 13 emulated the ability of heterogeneous R. sin-1 LPS to antagonize enteric LPS, providing evidence for the critical role of the gluconolactone moiety of R. sin-1 LPS in mediating this antagonistic effect. Compound 13 is the first example of a lipid A derivative that is devoid of phosphate but possesses antagonistic properties, making it an attractive lead compound for development of a drug to use in the treatment of Gram-negative septicemia.

  synthesis, lipid, lipid A, Rhizobia, Rhizobium, biological, evaluation

  NCBI PubMed ID: 12785841
  Publication DOI: 10.1021/ja029316s
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Correspondence: gjboons@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, The University of Georgia, 220 Riverbend Road, Athens 30602, USA
  Methods: 13C NMR, 1H NMR, PCR, TLC, ELISA, chemical synthesis, chemical methods, MALDI-TOF MS, TNF-a assays, biological assays
  
   
  
  Rhizobium sp. sin-1
  CSDB ID 31390 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1898
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772

• Article ID: 100
  Therisod H, Monteiro MA, Perry MB, Caroff M "Helicobacter mustelae lipid A structure differs from that of Helicobacter pylori" - FEBS Letters 499(1-2) (2001) 1-5
  

  The lipid A structure of the Gram-negative bacterium Helicobacter mustelae, a ferret gastric pathogen responsible for the onset of gastric diseases in its host, was investigated. Two variant lipid A structures were found in the same strain. One structure contained a bisphosphorylated β-(1→6)-linked D-glucosamine backbone disaccharide with hydroxytetradecanoic acid in amide linkages. Unlike the structure described for the lipid A of the related human Helicobacter pylori gastric pathogen, which contains a C1 phosphate moiety, this lipid A presented phosphate groups at both the C1 and C4' positions, and contained no octadecanoyl fatty acid, which is present in H. pylori. The second lipid A structure had a different fatty acid composition in that 3-OH C(16) replaced most of the amide-linked 3-OH C(14).

  structure, lipid A, endotoxin, Helicobacter mustelae, Helicobacter pylori

  NCBI PubMed ID: 11418100
  Publication DOI: 10.1016/S0014-5793(01)02496-6
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: martine.caroff@bbmpc.u-psud.fr
  Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Université de Paris-Sud, Orsay, France, Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON, Canada
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, TLC, 31P NMR, GC, MALDI-TOF MS, composition analysis, PD-MS, NMR-1D
  
   
  
  Helicobacter mustelae ATCC 43772
  CSDB ID 31385 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 105
  Toman R, Hussein A, Palkovic P, Ftacek P "Structural properties of lipopolysaccharides from Coxiella burnetii strains Henzerling and S" - Annals of the New York Academy of Sciences 990(563) (2003) 563-567
  

  no abstract

  Lipopolysaccharide, structure, Coxiella burnetii, isolation, chemical composition

  NCBI PubMed ID: 12860690
  Journal NLM ID: 7506858
  Publisher: New York Academy of Sciences
  Correspondence: virutoma@savba.sk
  Institutions: Institute of Virology, Slovak Academy of Sciences, 845 05 Bratislava, Slovak Republic
  Methods: GC-MS, SDS-PAGE, GC, MALDI-TOF MS, composition analysis, methanolysis
  
   
  
  Coxiella burnetii Henzerling
  CSDB ID 5213 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 105
  Toman R, Hussein A, Palkovic P, Ftacek P "Structural properties of lipopolysaccharides from Coxiella burnetii strains Henzerling and S" - Annals of the New York Academy of Sciences 990(563) (2003) 563-567
  

  no abstract

  Lipopolysaccharide, structure, Coxiella burnetii, isolation, chemical composition

  NCBI PubMed ID: 12860690
  Journal NLM ID: 7506858
  Publisher: New York Academy of Sciences
  Correspondence: virutoma@savba.sk
  Institutions: Institute of Virology, Slovak Academy of Sciences, 845 05 Bratislava, Slovak Republic
  Methods: GC-MS, SDS-PAGE, GC, MALDI-TOF MS, composition analysis, methanolysis
  
   
  
  Coxiella burnetii S
  CSDB ID 31382 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 2001.4
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 156
  Vedam V, Kannenberg EL, Haynes JG, Sherrier DJ, Datta A, Carlson RW "A Rhizobium leguminosarum acpXL mutant produces lipopolysaccharide lacking 27-hydroxyoctacosanoic acid" - Journal of Bacteriology 185(6) (2003) 1841-1850
  

  The structure of the lipid A from Rhizobium etli and Rhizobium leguminosarum lipopolysaccharides (LPSs) lacks phosphate and contains a galacturonosyl residue at its 4' position, an acylated 2-aminogluconate in place of the proximal glucosamine, and a very long chain omega-1 hydroxy fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0). The 27OHC28:0 moiety is common in lipid A's among members of the Rhizobiaceae and also among a number of the facultative intracellular pathogens that form chronic infections, e.g., Brucella abortus, Bartonella henselae, and Legionella pneumophila. In this paper, a mutant of R. leguminosarum was created by placing a kanamycin resistance cassette within acpXL, the gene which encodes the acyl carrier protein for 27OHC28:0. The result was an LPS containing a tetraacylated lipid A lacking 27OHC28:0. A small amount of the mutant lipid A may contain an added palmitic acid residue. The mutant is sensitive to changes in osmolarity and an increase in acidity, growth conditions that likely occur in the nodule microenvironment. In spite of the probably hostile microenvironment of the nodule, the acpXL mutant is still able to form nitrogen-fixing root nodules even though the appearance and development of nodules are delayed. Therefore, it is possible that the acpXL mutant has a host-inducible mechanism which enables it to adapt to these physiological changes.

  Lipopolysaccharide, lipid A, Rhizobium etli, Rhizobium leguminosarum

  NCBI PubMed ID: 12618448
  Publication DOI: 10.1128/JB.185.6.1841-1850.2003
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Carbohydrate Research Center, University of Georgia Complex, Athens, GA, USA, Department of Microbiology and Biotechnology, University of Tubingen, D072076 Tubingen, Germany, Department of Plant and Soil Sciences, University of Delaware, Newark, Delaware 19717
  Methods: GC-MS, mild acid hydrolysis, DOC-PAGE, GC, MALDI-TOF MS, composition analysis, genetic methods
  
   
  
  Rhizobium etli, Rhizobium leguminosarum bv. viciae 3841
  CSDB ID 31367 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1710.4
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 156
  Vedam V, Kannenberg EL, Haynes JG, Sherrier DJ, Datta A, Carlson RW "A Rhizobium leguminosarum acpXL mutant produces lipopolysaccharide lacking 27-hydroxyoctacosanoic acid" - Journal of Bacteriology 185(6) (2003) 1841-1850
  

  The structure of the lipid A from Rhizobium etli and Rhizobium leguminosarum lipopolysaccharides (LPSs) lacks phosphate and contains a galacturonosyl residue at its 4' position, an acylated 2-aminogluconate in place of the proximal glucosamine, and a very long chain omega-1 hydroxy fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0). The 27OHC28:0 moiety is common in lipid A's among members of the Rhizobiaceae and also among a number of the facultative intracellular pathogens that form chronic infections, e.g., Brucella abortus, Bartonella henselae, and Legionella pneumophila. In this paper, a mutant of R. leguminosarum was created by placing a kanamycin resistance cassette within acpXL, the gene which encodes the acyl carrier protein for 27OHC28:0. The result was an LPS containing a tetraacylated lipid A lacking 27OHC28:0. A small amount of the mutant lipid A may contain an added palmitic acid residue. The mutant is sensitive to changes in osmolarity and an increase in acidity, growth conditions that likely occur in the nodule microenvironment. In spite of the probably hostile microenvironment of the nodule, the acpXL mutant is still able to form nitrogen-fixing root nodules even though the appearance and development of nodules are delayed. Therefore, it is possible that the acpXL mutant has a host-inducible mechanism which enables it to adapt to these physiological changes.

  Lipopolysaccharide, lipid A, Rhizobium etli, Rhizobium leguminosarum

  NCBI PubMed ID: 12618448
  Publication DOI: 10.1128/JB.185.6.1841-1850.2003
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Carbohydrate Research Center, University of Georgia Complex, Athens, GA, USA, Department of Microbiology and Biotechnology, University of Tubingen, D072076 Tubingen, Germany, Department of Plant and Soil Sciences, University of Delaware, Newark, Delaware 19717
  Methods: GC-MS, mild acid hydrolysis, DOC-PAGE, GC, MALDI-TOF MS, composition analysis, genetic methods
  
   
  
  Rhizobium leguminosarum bv. viciae 3841
  CSDB ID 31368 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1493.2 [M-H]-
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 156
  Vedam V, Kannenberg EL, Haynes JG, Sherrier DJ, Datta A, Carlson RW "A Rhizobium leguminosarum acpXL mutant produces lipopolysaccharide lacking 27-hydroxyoctacosanoic acid" - Journal of Bacteriology 185(6) (2003) 1841-1850
  

  The structure of the lipid A from Rhizobium etli and Rhizobium leguminosarum lipopolysaccharides (LPSs) lacks phosphate and contains a galacturonosyl residue at its 4' position, an acylated 2-aminogluconate in place of the proximal glucosamine, and a very long chain omega-1 hydroxy fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0). The 27OHC28:0 moiety is common in lipid A's among members of the Rhizobiaceae and also among a number of the facultative intracellular pathogens that form chronic infections, e.g., Brucella abortus, Bartonella henselae, and Legionella pneumophila. In this paper, a mutant of R. leguminosarum was created by placing a kanamycin resistance cassette within acpXL, the gene which encodes the acyl carrier protein for 27OHC28:0. The result was an LPS containing a tetraacylated lipid A lacking 27OHC28:0. A small amount of the mutant lipid A may contain an added palmitic acid residue. The mutant is sensitive to changes in osmolarity and an increase in acidity, growth conditions that likely occur in the nodule microenvironment. In spite of the probably hostile microenvironment of the nodule, the acpXL mutant is still able to form nitrogen-fixing root nodules even though the appearance and development of nodules are delayed. Therefore, it is possible that the acpXL mutant has a host-inducible mechanism which enables it to adapt to these physiological changes.

  Lipopolysaccharide, lipid A, Rhizobium etli, Rhizobium leguminosarum

  NCBI PubMed ID: 12618448
  Publication DOI: 10.1128/JB.185.6.1841-1850.2003
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Carbohydrate Research Center, University of Georgia Complex, Athens, GA, USA, Department of Microbiology and Biotechnology, University of Tubingen, D072076 Tubingen, Germany, Department of Plant and Soil Sciences, University of Delaware, Newark, Delaware 19717
  Methods: GC-MS, mild acid hydrolysis, DOC-PAGE, GC, MALDI-TOF MS, composition analysis, genetic methods
  
   
  
  Rhizobium leguminosarum bv. viciae 22
  CSDB ID 31369 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1230.6 [M-H]-
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 156
  Vedam V, Kannenberg EL, Haynes JG, Sherrier DJ, Datta A, Carlson RW "A Rhizobium leguminosarum acpXL mutant produces lipopolysaccharide lacking 27-hydroxyoctacosanoic acid" - Journal of Bacteriology 185(6) (2003) 1841-1850
  

  The structure of the lipid A from Rhizobium etli and Rhizobium leguminosarum lipopolysaccharides (LPSs) lacks phosphate and contains a galacturonosyl residue at its 4' position, an acylated 2-aminogluconate in place of the proximal glucosamine, and a very long chain omega-1 hydroxy fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0). The 27OHC28:0 moiety is common in lipid A's among members of the Rhizobiaceae and also among a number of the facultative intracellular pathogens that form chronic infections, e.g., Brucella abortus, Bartonella henselae, and Legionella pneumophila. In this paper, a mutant of R. leguminosarum was created by placing a kanamycin resistance cassette within acpXL, the gene which encodes the acyl carrier protein for 27OHC28:0. The result was an LPS containing a tetraacylated lipid A lacking 27OHC28:0. A small amount of the mutant lipid A may contain an added palmitic acid residue. The mutant is sensitive to changes in osmolarity and an increase in acidity, growth conditions that likely occur in the nodule microenvironment. In spite of the probably hostile microenvironment of the nodule, the acpXL mutant is still able to form nitrogen-fixing root nodules even though the appearance and development of nodules are delayed. Therefore, it is possible that the acpXL mutant has a host-inducible mechanism which enables it to adapt to these physiological changes.

  Lipopolysaccharide, lipid A, Rhizobium etli, Rhizobium leguminosarum

  NCBI PubMed ID: 12618448
  Publication DOI: 10.1128/JB.185.6.1841-1850.2003
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Carbohydrate Research Center, University of Georgia Complex, Athens, GA, USA, Department of Microbiology and Biotechnology, University of Tubingen, D072076 Tubingen, Germany, Department of Plant and Soil Sciences, University of Delaware, Newark, Delaware 19717
  Methods: GC-MS, mild acid hydrolysis, DOC-PAGE, GC, MALDI-TOF MS, composition analysis, genetic methods
  
   
  
  Rhizobium leguminosarum bv. viciae 22
  CSDB ID 31370 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772

• Article ID: 180
  Vinogradov E, Perry MB, Conlan JW "Structural analysis of Francisella tularensis lipopolysaccharide" - European Journal of Biochemistry 269(24) (2002) 6112-6118
  

  The structure of the lipid A and core region of the lipopolysaccharide (LPS) from Francisella tularensis (ATCC 29684) was analysed using NMR, mass spectrometry and chemical methods. The LPS contains a β-GlcN-(1-6)-GlcN lipid A backbone, but has a number of unusual structural features; it apparently has no substituent at O-1 of the reducing end GlcN residue in the lipid part in the major part of the population, no substituents at O-3 and O-4 of β-GlcN, and no substituent at O-4 of the Kdo residue. The largest oligosaccharide, isolated after strong alkaline deacylation of NaBH4 reduced LPS had the following structure: where ∆-GalNA-(1-3)-β-QuiNAc represents a modified fragment of the O-chain repeating unit. Two shorter oligosaccharides lacking the O-chain fragment were also identified. A minor amount of the disaccharide β-GlcN-(1-6)-α-GlcN-1-P was isolated from the same reaction mixture, indicating the presence of free lipid A, unsubstituted by Kdo and with phosphate at the reducing end. The lipid A, isolated from the products of mild acid hydrolysis, had the structure 2-N-(3-O-acyl4-acyl2)-β-GlcN-(1-6)-2-N-acyl1-3-O-acyl3-GlcN where acyl1, acyl2 and acyl3 are 3-hydroxyhexadecanoic or 3-hydroxyoctadecanoic acids, acyl4 is tetradecanoic or (minor) hexadecanoic acids. No phosphate substituents were found in this compound. OH-1 of the reducing end glucosamine, and OH-3 and OH-4 of the nonreducing end glucosamine residues were not substituted. LPS of F. tularensis exhibits unusual biological properties, including low endoxicity, which may be related to its unusual lipid A structure.

  Lipopolysaccharide, NMR, LPS, oligosaccharide, structure, core, structural, repeating unit, analysis, chain, Kdo, lipid, lipid A, Oligosaccharides, spectrometry, structural analysis, chemical, core region, region, mass spectrometry, reduced, modified, method, alkaline, backbone, O-chain, fragment, population, methods, deacylation, disaccharide, Francisella tularensis, reducing, reducing end

  NCBI PubMed ID: 12473106
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: evguenii.vinogradov@nrc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
  Methods: NMR-2D, NMR, chemical methods, MS
  
   
  
  Francisella tularensis ATCC 29684
  CSDB ID 337 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1933.1
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531,IEDB_176772

• Article ID: 466
  Silipo A, Molinaro A, Cescutti P, Bedini E, Rizzo R, Parrilli M, Lanzetta R "Complete structural characterization of the lipid A fraction of a clinical strain of B. cepacia genomovar I lipopolysaccharide" - Glycobiology 15(5) (2005) 561-570
  

  Burkholderia cepacia, a Gram negative bacterium ubiquitous in the environment, is a plant pathogen causing soft rot of onions. This microorganism has recently emerged as a life-threatening multiresistant pathogen in cystic fibrosis patients. An important virulence factor of B. cepacia is the lipopolysaccharide fraction. Clinical isolates and environmental strains possess LPS of high inflammatory nature which induces a high level production of cytokines. For the first time, the complete structure of the lipid A components isolated from the lipopolysaccharide fraction of a clinical strain of Burkholderia cepacia is herein described. The structural studies carried out by selective chemical degradations, mass spectrometry and NMR spectroscopy revealed multiple species differing in the acylation and in the phosphorylation patterns. The highest mass species was identified as a penta-acylated tetrasaccharide backbone containing two phosphoryl-arabinosamine residues in addition to the archetypal glucosamine disaccharide [Arap4N-L-β-1-P→4-β-D-GlcpN-(1→6)-α-D-GlcpN-1→P-1-β-L-Arap4N] . Lipid A fatty acids substitution was also described, with two 3-hydroxytetradecanoic acids 14:0 (3-OH) in ester linkage, and two 3-hydroxyhexadecanoic acids 16:0 (3-OH) in amide-linkage, one of which was substituted by a secondary a 14:0 residue at its C-3. Other lipid A species present in the mixture and exhibiting lower molecular weight lacked one or both β-L-Arap4N residues.

  Lipopolysaccharide, LPS, Burkholderia, Burkholderia cepacia, lipid A, NMR spectroscopy, mass spectrometry

  NCBI PubMed ID: 15610978
  Publication DOI: 10.1093/glycob/cwi029
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: molinaro@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, composition analysis, methanolysis
  
   
  
  Burkholderia cepacia
  CSDB ID 8945 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1576.5
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531,IEDB_176772

• Article ID: 466
  Silipo A, Molinaro A, Cescutti P, Bedini E, Rizzo R, Parrilli M, Lanzetta R "Complete structural characterization of the lipid A fraction of a clinical strain of B. cepacia genomovar I lipopolysaccharide" - Glycobiology 15(5) (2005) 561-570
  

  Burkholderia cepacia, a Gram negative bacterium ubiquitous in the environment, is a plant pathogen causing soft rot of onions. This microorganism has recently emerged as a life-threatening multiresistant pathogen in cystic fibrosis patients. An important virulence factor of B. cepacia is the lipopolysaccharide fraction. Clinical isolates and environmental strains possess LPS of high inflammatory nature which induces a high level production of cytokines. For the first time, the complete structure of the lipid A components isolated from the lipopolysaccharide fraction of a clinical strain of Burkholderia cepacia is herein described. The structural studies carried out by selective chemical degradations, mass spectrometry and NMR spectroscopy revealed multiple species differing in the acylation and in the phosphorylation patterns. The highest mass species was identified as a penta-acylated tetrasaccharide backbone containing two phosphoryl-arabinosamine residues in addition to the archetypal glucosamine disaccharide [Arap4N-L-β-1-P→4-β-D-GlcpN-(1→6)-α-D-GlcpN-1→P-1-β-L-Arap4N] . Lipid A fatty acids substitution was also described, with two 3-hydroxytetradecanoic acids 14:0 (3-OH) in ester linkage, and two 3-hydroxyhexadecanoic acids 16:0 (3-OH) in amide-linkage, one of which was substituted by a secondary a 14:0 residue at its C-3. Other lipid A species present in the mixture and exhibiting lower molecular weight lacked one or both β-L-Arap4N residues.

  Lipopolysaccharide, LPS, Burkholderia, Burkholderia cepacia, lipid A, NMR spectroscopy, mass spectrometry

  NCBI PubMed ID: 15610978
  Publication DOI: 10.1093/glycob/cwi029
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: molinaro@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, composition analysis, methanolysis
  
   
  
  Burkholderia cepacia
  CSDB ID 10622 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531

• Article ID: 467
  Silipo A, De Castro C, Lanzetta R, Molinaro A, Parrilli M "Full structural characterization of the lipid A components from the Agrobacterium tumefaciens strain C58 lipopolysaccharide fraction" - Glycobiology 14(9) (2004) 805-815
  

  For the first time, the complete structure of the lipid A from the lipopolysaccharide of an Agrobacterium species is here reported. In particular, the structure of the lipid A from A. tumefaciens strain C58, a soil pathogen bacterium strictly related to Rhizobiaceae, was determined. The structural study, carried out by chemical analysis, mass spectrometry, and nuclear magnetic resonance spectroscopy, revealed that lipid A fraction consisted of a mixture of species all sharing the bis-phosphorylated glucosamine disaccharide backbone that could be designated in two main structural motifs, according to the acylation pattern. The main species was a penta-acylated lipid A bearing two unsubstituted 14:0 (3-OH) fatty acids in ester linkage and two 16:0 (3-OH) in amide linkage; the one on GlcN II was O-acylated by a long chain fatty acid, 28:0 (27-OH). This in turn was esterified by a 3-hydroxy-butyroyl residue at its hydroxy group. The second species, in lesser amounts, was identified as a tetra-acylated lipid A and lacked the 14:0 (3-OH) residue on GlcN I. Other species deriving from these two lacked a phosphate group or 3-hydroxy-butyroyl residue or otherwise carried a 26:0 (25-OH) as long chain fatty acid. The lipid A structure of phytopathogen A. tumefaciens strain C58 presents deep structural analogies with lipid A of symbiotic Rhizobium, and the hypothesis is advanced that it can be a strategy of the bacterium to escape or attenuate the plant response

  Lipopolysaccharide, lipid A, NMR spectroscopy, Agrobacterium tumefaciens, MALDI-TOF mass spectrometry

  NCBI PubMed ID: 15159382
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: molinaro@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia 4, 80126 Napoli, Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, sugar analysis, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, methanolysis
  
   
  
  Agrobacterium tumefaciens C58
  CSDB ID 8946 (all data & tools)