Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534865

• Article ID: 36
  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
  
   
  
  Chlamydia trachomatis
  CSDB ID 31470 (all data & tools)

Show legend Show as text

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

• Article ID: 36
  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)

Show legend Show as text

Structure type: oligomer ; 1295
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 99
  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 pylori
  CSDB ID 31383 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_137340,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 104
  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_137340,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 104
  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
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_130650,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 495
  Trent MS "Biosynthesis, transport, and modification of lipid A" - Biochemistry and Cell Biology 82(1) (2004) 71-86
  

  Lipopolysaccharide (LPS) is the major surface molecule of Gram-negative bacteria and consists of three distinct structural domains: O-antigen, core, and lipid A. The lipid A (endotoxin) domain of LPS is a unique, glucosamine-based phospholipid that serves as the hydrophobic anchor of LPS and is the bioactive component of the molecule that is associated with Gram-negative septic shock. The structural genes encoding the enzymes required for the biosynthesis of Escherchia coli lipid A have been identified and characterized. Lipid A is often viewed as a constitutively synthesized structural molecule. However, determination of the exact chemical structures of lipid A from diverse Gram-negative bacteria shows that the molecule can be further modified in response to environmental stimuli. These modifications have been implicated in virulence of pathogenic Gram-negative bacteria and represent one of the molecular mechanisms of microbial surface remodeling used by bacteria to help evade the innate immune response. The intent of this review is to discuss the enzymatic machinery involved in the biosynthesis of lipid A, transport of the molecule, and finally, those enzymes involved in the modification of its structure in response to environmental stimuli.

  lipopolysaccharides, lipide A, endotoxine, membrane externe, MsbA

  NCBI PubMed ID: 15052329
  Journal NLM ID: 8606068
  Publisher: Ottawa: National Research Council of Canada
  Correspondence: trentms@mailetsu.edu
  Institutions: Department of Microbiology, Box 70579, East Tennessee State University, J.H. Quillen College of Medicine, Johnson City, TN 37614, U.S.A.
  
   
  
  Helicobacter pylori
  CSDB ID 31343 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_137340,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534865

• Article ID: 1434
  Alexander C, Zähringer U "Chemical structure of lipid A - the primary immunomodulatory center of bacterial lipopolysaccharides" - Trends in Glycoscience and Glycotechnology 14(76) (2002) 69-86
  

  Lipopolysaccharides (LPS) are the major outer surface membrane components expressed by the vast majority of Gram-negative bacteria and have been identified to be extremely strong stimulators of innate or natural immunity in diverse eukaryotic species ranging from insects or plants to humans. Due to early observations on the induction of severe pathological forms of immunoactivation such as septic shock this class of bacterial surface molecules has been termed ‘endotoxins’. By combination of chemical analysis, mass spectrometry and NMR techniques, the chemical structures of LPS from a variety of Gram-negative bacteria have been characterized in detail. LPS consist of an extracellular poly- or oligosaccharide region that is anchored in the outer bacterial membrane by a specific glycolipid termed lipid A. The lipid A component has been identified to be the primary immunostimulatory center of LPS. An overview of major types of lipid A structures recently established is given, thus completing and updating previous reviews (1, 2). In the present review central structure-bioactivity-correlations are discussed with respect to immunoactivation of the mammalian phagocyte system. In addition to the classical group of strongly agonistic (highly endotoxic) forms of lipid A, several natural or synthetic lipid A structures have been identified that display comparatively low or even no phagocyte activation for a given mammalian species. Some members of the latter more heterogeneous group are capable to antagonize the effects of strongly stimulatory LPS/lipid A. LPS of Gram-negative bacteria have been found to express a certain degree of structural diversity with respect to three structural elements: the glycosyl part of lipid A (lipid A backbone), the number, charge and linkage of polar head-group substituents, and the number, position and chemical nature of various acyl residues directly or indirectly linked to the lipid A backbone. Among all these structural variations, the acylation pattern has been found to encode mostly for its strong agonistic or antagonistic immunostimulatory activities in various biosystems.

  Lipopolysaccharide, lipid A, variability, antagonists, immunomodulatory activity

  Publication DOI: 10.4052/tigg.14.69
  Journal NLM ID: 9425898
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Research Center Borstel, Center of Medicine and Bio-Sciences Department of Immunochemistry and Biochemical Microbiology
  
   
  
  Chlamydia trachomatis
  CSDB ID 31312 (all data & tools)

Show legend Show as text

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

• Article ID: 1434
  Alexander C, Zähringer U "Chemical structure of lipid A - the primary immunomodulatory center of bacterial lipopolysaccharides" - Trends in Glycoscience and Glycotechnology 14(76) (2002) 69-86
  

  Lipopolysaccharides (LPS) are the major outer surface membrane components expressed by the vast majority of Gram-negative bacteria and have been identified to be extremely strong stimulators of innate or natural immunity in diverse eukaryotic species ranging from insects or plants to humans. Due to early observations on the induction of severe pathological forms of immunoactivation such as septic shock this class of bacterial surface molecules has been termed ‘endotoxins’. By combination of chemical analysis, mass spectrometry and NMR techniques, the chemical structures of LPS from a variety of Gram-negative bacteria have been characterized in detail. LPS consist of an extracellular poly- or oligosaccharide region that is anchored in the outer bacterial membrane by a specific glycolipid termed lipid A. The lipid A component has been identified to be the primary immunostimulatory center of LPS. An overview of major types of lipid A structures recently established is given, thus completing and updating previous reviews (1, 2). In the present review central structure-bioactivity-correlations are discussed with respect to immunoactivation of the mammalian phagocyte system. In addition to the classical group of strongly agonistic (highly endotoxic) forms of lipid A, several natural or synthetic lipid A structures have been identified that display comparatively low or even no phagocyte activation for a given mammalian species. Some members of the latter more heterogeneous group are capable to antagonize the effects of strongly stimulatory LPS/lipid A. LPS of Gram-negative bacteria have been found to express a certain degree of structural diversity with respect to three structural elements: the glycosyl part of lipid A (lipid A backbone), the number, charge and linkage of polar head-group substituents, and the number, position and chemical nature of various acyl residues directly or indirectly linked to the lipid A backbone. Among all these structural variations, the acylation pattern has been found to encode mostly for its strong agonistic or antagonistic immunostimulatory activities in various biosystems.

  Lipopolysaccharide, lipid A, variability, antagonists, immunomodulatory activity

  Publication DOI: 10.4052/tigg.14.69
  Journal NLM ID: 9425898
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Research Center Borstel, Center of Medicine and Bio-Sciences Department of Immunochemistry and Biochemical Microbiology
  
   
  
  Aquifex pyrophilus
  CSDB ID 31314 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 1479
  Sakai Y, Oikawa M, Yoshizaki H, Ogawa T, Suda Y, Fukase K, Kusumoto S "Synthesis of Helicobacter pylori lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group" - Tetrahedron Letters 41(35) (2000) 6843-6847
  

  Synthesis of lipid A 1 isolated from Helicobacter pylori strain 206-1 has been achieved in 2.2% total yield through 14 steps from d-glucosamine by employing a p-(trifluoromethyl)benzyl group for protection of the hydroxy group on the 3-hydroxy fatty acid residue. The synthetic specimen was identical with the natural counterpart in chromatographic, spectroscopic, and biological aspects. A structural analogue 2 which lacks the ethanolamine residue of 1 was also synthesized, and 2 was found to exhibit less potent IL-1β-inducing activity than 1.

  synthesis, lipopolysaccharides, lipid, lipid A, Helicobacter pylori, Helicobacter, IL-1b induction

  Publication DOI: 10.1016/S0040-4039(00)01158-8
  Journal NLM ID: 2984819R
  Publisher: Elsevier
  Correspondence: moik@chem.sci.osaka-u.ac.jp
  Institutions: Nutrition Research Institute, Otsuka Pharmaceutical Factory, Inc., Muya-Cho, Naruto, Tokushima 772-8601, Japan, Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama-cho 1-1, Toyonaka, Osaka 560-0043, Japan, Department of Oral Microbiology, Asahi University School of Dentistry, 1851-1 Hozumi, Hozumi-cho, Motosu-gun, Gifu 501-0296, Japan
  Methods: 1H NMR, ESI-MS, chemical synthesis, chemical methods
  
   
  
  Helicobacter pylori 206-1
  CSDB ID 4399 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 1479
  Sakai Y, Oikawa M, Yoshizaki H, Ogawa T, Suda Y, Fukase K, Kusumoto S "Synthesis of Helicobacter pylori lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group" - Tetrahedron Letters 41(35) (2000) 6843-6847
  

  Synthesis of lipid A 1 isolated from Helicobacter pylori strain 206-1 has been achieved in 2.2% total yield through 14 steps from d-glucosamine by employing a p-(trifluoromethyl)benzyl group for protection of the hydroxy group on the 3-hydroxy fatty acid residue. The synthetic specimen was identical with the natural counterpart in chromatographic, spectroscopic, and biological aspects. A structural analogue 2 which lacks the ethanolamine residue of 1 was also synthesized, and 2 was found to exhibit less potent IL-1β-inducing activity than 1.

  synthesis, lipopolysaccharides, lipid, lipid A, Helicobacter pylori, Helicobacter, IL-1b induction

  Publication DOI: 10.1016/S0040-4039(00)01158-8
  Journal NLM ID: 2984819R
  Publisher: Elsevier
  Correspondence: moik@chem.sci.osaka-u.ac.jp
  Institutions: Nutrition Research Institute, Otsuka Pharmaceutical Factory, Inc., Muya-Cho, Naruto, Tokushima 772-8601, Japan, Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama-cho 1-1, Toyonaka, Osaka 560-0043, Japan, Department of Oral Microbiology, Asahi University School of Dentistry, 1851-1 Hozumi, Hozumi-cho, Motosu-gun, Gifu 501-0296, Japan
  Methods: 1H NMR, ESI-MS, chemical synthesis, chemical methods
  
   
  
  Helicobacter pylori 206-1
  CSDB ID 31301 (all data & tools)
• Article ID: 1486
  Suda Y, Ogawa T, Kashihara W, Oikawa M, Shimoyama T, Hayashi T, Tamura T, Kusumoto S "Chemical structure of lipid A from Helicobacter pylori strain 206-1 lipopolysaccharide" - Journal of Biochemistry 121(6) (1997) 1129-1133
  

  The chemical structure of a novel lipid A, which was obtained as a major component from lipopolysaccharide of Helicobacter pylori strain 206-1, was determined to be a glucosamine β(1-6) disaccharide 1-(2-aminoethyl)phosphate acylated by (R)-3-hydroxyoctadecanoic acid and (R)-3-(octadecanoyloxy)octadecanoic acid at the 2- and 2'-position, respectively. The absence of a phosphoryl group at the 4'-position and fatty acyl groups at the 3- and 3'-position, and the stoichiometric presence of 2-aminoethyl phosphate at the 1-position are unique features, distinguishing it from the lipid A of enterobacteria.

  Lipopolysaccharide, structure, lipid A, Helicobacter pylori, MS

  NCBI PubMed ID: 9354387
  Journal NLM ID: 0376600
  Publisher: Japanese Biochemical Society
  Correspondence: ysuda@chem.sci.osaka-u.ac.jp
  Institutions: Department of Chemistry, Graduate School of Science, Osaka University, Department of Oral Microbiology, Osaka University Dental School, Department of Internal Medicine, Hyogo College of Medicine, Nishinomiya, Department of Bacteriology, Hyogo College of Medicine
  Methods: 1H NMR, SDS-PAGE, TLC, 31P NMR, ESI-MS, acid hydrolysis, ESI-MS/MS, composition analysis, LSI-MS
  
   
  
  Helicobacter pylori 206-1
  CSDB ID 4965 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 1485
  Suda T, Kim Y, Ogawa T, Yasui N, Hasegawa Y, Kashihara W, Shimoyama T, Aoyama K, Nagata K, Tamura T, Kusumoto S "Chemical structure and biological activity of a lipid A component from Helicobacter pylori strain 206" - Journal of Endotoxin Research 7(2) (2001) 95-104
  

  The chemical structure of a lipid A, which was obtained as a minor component from lipopolysaccharide of Helicobacter pylori strain 206-1, was determined to be a glucosamine β-(1-6) disaccharide 1-(2-aminoethyl)phosphate acylated by (R)-3-hydroxyoctadecanoic acid, (R)-3- hydroxyhexadecanoic acid, and (R)-3-(octadecanoyloxy)octadecanoic acid at the 2-, 3- and 2'-positions, respectively. Compared with the other major lipid A from the same strain, which was previously reported [Suda Y, Ogawa T, Kashihara W et al. Chemical structure of lipid A from Helicobacter pylori strain 206-1 lipopolysaccharide. J Biochem 1997; 121: 1129--1133], the structure was very similar with one exception. An (R)-3-hydroxyhexadecanoic acid was present at the 3-position of the novel lipid A component. The structure is apparently identical to one of the proposals by Moran et al. [Moran AP, Lindner B, Walsh EJ. Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides. J Bacteriol 1997; 179: 6453--6463], who concluded the same structure as the so-called major lipid A from the H. pylori strain NCTC 11637 but without isolating a homogeneous component. The endotoxic properties and pro-inflammatory cytokine-inducing activities of this novel tetra-acyl type lipid A were lower than those of previously reported major tri-acyl type lipid A.

  structure, lipid A, chemical structure, biological activity, Helicobacter pylori, Helicobacter

  NCBI PubMed ID: 11521089
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Correspondence: ysuda@chem.sci.osaka-u.ac.jp
  Institutions: Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan, Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan, Department of Internal Medicine IV, Hyogo College of Medicine, Hyogo, Japan, Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan
  Methods: 1H NMR, FAB-MS, SDS-PAGE, TLC, 31P NMR, ESI-MS, acid hydrolysis, ESI-MS/MS, GC, biological assays, composition analysis, LSI-MS, cytokine assay
  
   
  
  Helicobacter pylori 206-1
  CSDB ID 4964 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 1490
  Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" - Book: Endotoxin in Health and Disease (1999) 93-114
  

  no abstract available

  lipopolysaccharides, core, structural analysis, lipid A, O-polysaccharide, endotoxin, stucture

  WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=false
  Publisher: New York, Marcel Dekker, Inc.
  Editors: Brade H, Opal SM, Vogel SN, Morrison DC
  Institutions: Research Center Borstel, Borstel, Germany
  
   
  
  Helicobacter pylori
  CSDB ID 31439 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864,IEDB_534865

• Article ID: 1490
  Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" - Book: Endotoxin in Health and Disease (1999) 93-114
  

  no abstract available

  lipopolysaccharides, core, structural analysis, lipid A, O-polysaccharide, endotoxin, stucture

  WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=false
  Publisher: New York, Marcel Dekker, Inc.
  Editors: Brade H, Opal SM, Vogel SN, Morrison DC
  Institutions: Research Center Borstel, Borstel, Germany
  
   
  
  Helicobacter pylori
  CSDB ID 31440 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534865

• Article ID: 1490
  Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" - Book: Endotoxin in Health and Disease (1999) 93-114
  

  no abstract available

  lipopolysaccharides, core, structural analysis, lipid A, O-polysaccharide, endotoxin, stucture

  WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=false
  Publisher: New York, Marcel Dekker, Inc.
  Editors: Brade H, Opal SM, Vogel SN, Morrison DC
  Institutions: Research Center Borstel, Borstel, Germany
  
   
  
  Chlamydia trachomatis
  CSDB ID 31457 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1783 [M-H]-
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534865

• Article ID: 1611
  Ferguson GP, Datta A, Carlson RW, Walker GC "Importance of unusually modified lipid A in Sinorhizobium stress resistance and legume symbiosis" - Molecular Microbiology 56(1) (2005) 68-80
  

  Sinorhizobium meliloti, a legume symbiont and Brucella abortus, a phylogenetically related mammalian pathogen, both require their BacA proteins to establish chronic intracellular infections in their respective hosts. The lipid A molecules of S. meliloti and B. abortus are unusually modified with a very-long-chain fatty acid (VLCFA; C > or = 28) and we discovered that BacA is involved in this unusual modification. This observation raised the possibility that the unusual lipid A modification could be crucial for the chronic infection of both S. meliloti and B. abortus. We investigated this by constructing and characterizing S. meliloti mutants in the lpxXL and acpXL genes, which encode an acyl transferase and acyl carrier protein directly involved in the biosynthesis of VLCFA-modified lipid A. Our analysis revealed that the unusually modified lipid A is important, but not crucial, for S. meliloti chronic infection and that BacA must have an additional function, which in combination with its observed effect on the lipid A in the free-living form of S. meliloti, is essential for the chronic infection. Additionally, we discovered that in the absence of VLCFAs, S. meliloti produces novel pentaacylated lipid A species, modified with unhydroxylated fatty acids, which are important for stress resistance.

  transferase, lipid A, symbiosis, Brucella abortus, Sinorhizobium meliloti, Sinorhizobium, acyltransferases, stress

  NCBI PubMed ID: 15773979
  Publication DOI: 10.1111/j.1365-2958.2005.04536.x
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Correspondence: G.Ferguson@ed.ac.uk; gwalker@mit.edu
  Institutions: Institute of Structural and Molecular Biology, School of Biological Sciences, University of Edinburgh, Edinburgh, EH9 3JR, UK, Biology Department, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA, Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA, Glycobiology Research and Training Center, Department of Molecular and Cellular Medicine, University of California, San Diego, La Jolla, CA 92093-0687, USA
  Methods: PCR, GC-MS, SDS-PAGE, DOC-PAGE, MALDI-TOF MS, biological assays, genetic methods
  
   
  
  Sinorhizobium meliloti acpXL
  CSDB ID 31277 (all data & tools)