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1. Compound ID: 2382
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a-Kdop-(2-8)-+ P-4)-+
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a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Trivial name: core-lipid A backbone, epitope J
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_135394,IEDB_137340,IEDB_140092,IEDB_141807,IEDB_150755,IEDB_150756,IEDB_150760,IEDB_150901,IEDB_150908,IEDB_151531,IEDB_151769
The structure is contained in the following publication(s):
- Article ID: 814
Holst O, Bock K, Brade L, Brade H "The structures of oligosaccharide bisphosphates isolated from the lipopolysaccharide of a recombinant Escherichia coli strain expressing the gene gseA [3-deoxy-D-manno-octulopyranosonic acid (Kdo) transferase] of Chlamydia psittaci 6BC" -
European Journal of Biochemistry 229 (1995) 194-200
The lipopolysaccharide from the recombinant strain Escherichia coli F515-140 containing the cloned gene gseA [3-deoxy-D-manno-octulopyranosonic acid (Kdo) transferase] from Chlamydia psittaci 6BC was isolated and sequentially de-O-acylated and de-N-acylated. The products were separated by high-performance anion-exchange chromatography into three fractions, two of which contained a single compound. Their structures were elucidated by high-field NMR spectroscopy as α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 1) (tetrasaccharide bisphosphate) [Holst, O., Broer, W., Thomas-Oates, J. E., Mamat, U. & Brade, H. (1993) Eur. J. Biochem. 214, 703-710] and α-Kdo-(2→4)-[α-Kdo-(2→8)-]-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 4) (hexasaccharide bisphosphate). The third fraction comprised two pentasaccharide bisphosphates, which could be separated by affinity chromatography using an immobilized monoclonal antibody specific for the trisaccharide α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo. The bound fraction was identified as α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 2) [Holst, O., Broer, W., Thomas-Oates, J. E., Mamat, U. & Brade, H. (1993) Eur. J. Biochem. 214, 703-710], whereas the unbound fraction was identified as α-Kdo-(2→4)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 3). This novel Kdo tetrasaccharide extends our knowledge on multifunctional Kdo transferases.
Lipopolysaccharide, LPS, oligosaccharide, structure, core, gene, strain, Escherichia, Escherichia coli, acid, Kdo, transferase, phosphate, Chlamydia, recombinant, bisphosphate, Chlamydia psittaci, gseA, HPLC
NCBI PubMed ID: 7744029Publication DOI: 10.1111/j.1432-1033.1995.0194l.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: oholst@fz-borstel.de
Institutions: Division of Biochemical Microbiology, Forschungsinstitut Borstel, Germany, Division of Biochemical Microbiology, Institut fur Experimentelle Biologie und Medizin, Forschungsinstitut Borstel, Germany, Department of Chemistry, Carisberg Laboratory, Copenhagen, Denmark
Methods: 13C NMR, 1H NMR, GLC-MS, 31P NMR, HPAEC, affinity chromatography
- Article ID: 1157
Rund S, Lindner B, Brade H, Holst O "Structural analysis of the lipopolysaccharide from Chlamydophila psittaci strain 6BC" -
European Journal of Biochemistry 267(18) (2000) 5717-5726
The lipopolysaccaride of Chlamydophila psittaci 6BC was isolated from tissue culture-grown elementary bodies using a modified phenol/water procedure followed by extraction with phenol/chloroform/light petroleum. Compositional analyses indicated the presence of 3-deoxy-Dmanno-oct-2-ulosonic acid, GlcN, organic bound phosphate and fatty acids in a molar ratio of approximately 3. 3 : 2 : 1.8 : 4.6. Deacylated lipopolysaccharide was obtained after successive microscale treatment with hydrazine and potassium hydroxide, and was then separated by high performance anion-exchange chromatography into two major fractions, the structures of which were determined by 600 MHz NMR spectroscopy as α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcpN-(1→6)-α-D-GlcpN 1,4'-bisphosphate and α-Kdo-(2→4)-[α-Kdo-(2→8)]-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcpN-(1→6)-α-D-GlcpN 1,4'-bisphosphate. The distribution of fatty acids in lipid A was determined by compositional analyses andmatrix-assisted laser desorption/ionization time-of-flight mass spectrometry experiments on lipid A and de-O-acylated lipid A. It was shown that the carbohydrate backbone of lipid A is replaced by a complex mixture of fatty acids, including long-chain and branched (R)-configured 3-hydroxy fatty acids, the latter being exclusively present in an amide linkage
Lipopolysaccharide, strain, structural, serotype, analysis, structural analysis, Chlamydophila psittaci, NMR spectroscopy, mass spectrometry
NCBI PubMed ID: 10971582Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: oholst@fz-borstel.de
Institutions: Divisions of Medical and Biochemical Microbiology and Biophysics, Research Center Borstel, Center for Medicine and Biosciences, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, MALDI-TOF MS
- Article ID: 1386
Brabetz W, Lindner B, Brade H "Comparative analyses of secondary gene products of 3-deoxy-D-manno-oct-2-ulosonic acid transferases from Chlamydiaceae in Escherichia coli K-12" -
European Journal of Biochemistry 267(17) (2000) 5458-5465
The waaA gene encoding the essential, lipopolysaccharide (LPS)-specific 3-deoxy-Dmanno-oct-2-ulosonic acid (Kdo) transferase was inactivated in the chromosome of a heptosyltransferase I and II deficient Escherichia coli K-12 strain by insertion of gene expression cassettes encoding the waaA genes of Chlamydia trachomatis, Chlamydophila pneumoniae or Chlamydophila psittaci. The three chlamydial Kdo transferases were able to complement the knockout mutation without changing the growth or multiplication behaviour. The LPS of the mutants were serologically and structurally characterized in comparison to the LPS of the parent strain using compositional analyses, high performance anion exchange chromatography, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and specific monoclonal antibodies. The data show that chlamydial Kdo transferases can replace in E. coli K-12 the host's Kdo transferase and retain the product specificities described in their natural background. In addition, we unequivocally proved that WaaA from C. psittaci transfers predominantly four Kdo residues to lipid A, forming a branched tetrasaccharide with the structure α-Kdo-(2→8)-[α-Kdo-(2→4)]-α-Kdo-(2→4)-α-Kdo.
Lipopolysaccharide, LPS, gene, Escherichia, Escherichia coli, 3-deoxy-D-manno-oct-2-ulosonic acid, acid, Kdo, transferase, transferases, Chlamydiaceae, genetic complementation, multifunctional 3-deoxy-D-manno-oct-2, product specificity, ulosonic acid transferases
NCBI PubMed ID: 10951204Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: wbrabetz@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Divizion of Medical and Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences,Borstel,Germany
- Article ID: 3825
Brooks CL, Müller-Loennies S, Borisova SN, Brade L, Kosma P, Hirama T, MacKenzie CR, Brade H, Evans SV "Antibodies raised against chlamydial lipopolysaccharide antigens reveal convergence in germline gene usage and differential epitope recognition" -
Biochemistry 49(3) (2010) 570-581
The structures of antigen-binding fragments from two related monoclonal antibodies have been determined to high resolution in the presence of several carbohydrate antigens raised against chlamydial lipopolysaccharide. With the exception of CDR H3, antibodies S54-10 and S73-2 are both derived from the same set of germline gene segments as the previously reported structures S25-2 and S45-18. Despite this similarity, the antibodies differ in specificity and the mechanism by which they recognize their cognate antigen. S54-10 uses an unrelated CDR H3 to recognize its antigen in a fashion analogous to S45-18; however, S73-2 recognizes the same antigen as S45-18 and S54-10 in a wholly unrelated manner. Together, these antibody-antigen structures provide snapshots into how the immune system uses the same set of inherited germline gene segments to generate multiple possible specificities that allow for differential recognition of epitopes and how unrelated CDR H3 sequences can result in convergent binding of clinically relevant bacterial antigens.
antibodies, epitope, recognition, antigens, Chlamydia, binding
NCBI PubMed ID: 20000757Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: hebra@fz-borstel.de; svevans@uvic.ca
Institutions: University of Victoria, Department of Biochemistry and Microbiology, PO Box 3055 STN CSC, Victoria, BC, Canada V8P 3P6
Methods: ELISA, serological methods, genetic methods, crystallization, surface plasmon resonance (SPR)
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2. Compound ID: 2655
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a-Kdop-(2-8)-+
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a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-1)-Allyl |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_130662,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_150756,IEDB_150901,IEDB_151531,IEDB_151769,IEDB_156486,IEDB_164045
The structure is contained in the following publication(s):
- Article ID: 905
Kosma P, Reiter A, Hofinger A, Brade L, Brade H "Synthesis of neoglycoproteins containing Kdo epitopes specific for Chlamydophila psittaci lipopolysaccharide" -
Journal of Endotoxin Research 6(1) (2000) 57-69
Lipopolysaccharide, synthesis, Kdo, epitope, epitopes, specific, neoglycoprotein, neoglycoproteins
Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: pkosma@edv2.boku.ac.at
Institutions: Department of Chemistry, University of Agricultural Sciences, Muthgasse, Vienna, Austria
Methods: NMR
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3. Compound ID: 3779
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a-Kdop-(2-8)-+
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a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2--/lipid A/ |
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Structure type: fragment of a bigger structure
Aglycon: lipid A
Trivial name: inner core
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_150901,IEDB_151769
The structure is contained in the following publication(s):
- Article ID: 1440
Gronow S, Brade H "Lipopolysaccharide biosynthesis: which steps do bacteria need to survive?" -
Journal of Endotoxin Research 7(1) (2001) 3-23
A detailed knowledge of LPS biosynthesis is of the utmost importance in understanding the function of the outer membrane of Gram-negative bacteria. The regulation of LPS biosynthesis affects many more compartments of the bacterial cell than the outer membrane and thus contributes to the understanding of the physiology of Gram-negative bacteria in general, on the basis of which only mechanisms of virulence and antibiotic resistance can be studied to find new targets for antibacterial treatment. The study of LPS biosynthesis is also an excellent example to demonstrate the limitations of 'genomics' and 'proteomics', since secondary gene products can be studied only by the combined tools of molecular genetics, enzymology and analytical structural biochemistry. Thus, the door to the field of 'glycomics' is opened.
Lipopolysaccharide, biosynthesis, lipopolysaccharides, LPS, metabolism, microbiology, lipopolysaccharide biosynthesis, gram negative bacteria, membrane
NCBI PubMed ID: 11521077Publication DOI: 10.1177/09680519010070010301Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: sgronow@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
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4. Compound ID: 3922
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a-Kdop-(2-8)-+
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a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_150901,IEDB_151769
The structure is contained in the following publication(s):
- Article ID: 1459
Holst O "Chemical structure of the core region of lipopolysaccharides - an update" -
Trends in Glycoscience and Glycotechnology 14(76) (2002) 87-103
Lipopolysaccharides (LPS) are the endotoxins of Gram-negative bacteria and very well known for their immunological, pharmacological and pathophysiological effects displayed in eucaryotic cells and organisms. To date, much emphasis has been put on the elucidation of the chemical structures of LPS and on their relation, or that of substructures, to the various biological effects. The lipid part of LPS, the lipid A, was proven to represent the toxic principle of endotoxin. However, lipid A toxicity depends strongly on its structure, and is influenced by a second region of LPS, the core region, that is covalently linked to lipid A. Also, the core region possesses immunogenic properties. Therefore, complete structural analyses of the core region and the comparison of its structures with biological features of LPS are of high importance for a better understanding of LPS action, and one prerequesite for strategies aimed at the treatment of endotoxicosis. In the past, quite a number of structures of the core regions from various Gram-negative bacteria were published and summarized in several overviews. The present review adds to this knowledge those structures that were published between October 1998 and December 2001.
lipopolysaccharides, heptose, Kdo, chemical structure, core region, tructure
Publication DOI: 10.4052/tigg.14.87Journal NLM ID: 9425898Correspondence: oholst@fz-borstel.de
Institutions: Structural Biochemistry, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
- Article ID: 3693
Gronow S, Lindner B, Brade H, Müller-Loennies S "Kdo-(2->8)-Kdo-(2->4)-Kdo but not Kdo-(2->4)-Kdo-(2->4)-Kdo is an acceptor for transfer of L-glycero-a-D-manno-heptose by Escherichia coli heptosyltransferase I (WaaC)" -
Innate Immunity 15(1) (2009) 13-23
Early steps in the biosynthesis of lipopolysaccharide (LPS) involve the transfer of 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (Kdo) to lipid A. Whereas Kdo transferases (WaaA) of Escherichia coli generate a (2→4)-linked Kdo disaccharide, Chlamydiae contain tri- or tetra-functional WaaA generating oligosaccharides with (2→8)- and (2→4)-linkages between Kdo. It has been suggested that the transfer of L-glycero-α-D-manno-heptose (Hep) to Kdo by an E. coli WaaC may not be possible in the presence of (2→8)-linked Kdo. E. coli double-mutants deficient in heptosyltransferases I (waaC) and II (waaF) and expressing waaA of Chlamydiae instead of their own, make Chlamydia-type Kdo oligosaccharides which are attached to an E. coli lipid A. Using such strains expressing waaA of Chlamydophila pneumoniae, Chlamydophila psittaci, or Chlamydia trachomatis, we have studied the effect of E. coli waaC gene expression on LPS structure. Structural analyses revealed the formation of two novel oligosaccharides Hep-(1→5)[Kdo-(2→4)]-Kdo and Hep-(1→5)[Kdo-(2→8)-Kdo-(2→4)]-Kdo showing that Hep is transferred in the presence of (2→8)-linked Kdo. Surprisingly, the transfer of Hep onto Kdo-(2→4)-Kdo-(2→4)-Kdo did not occur, despite the fact that Hep-(1→5)[Kdo-(2→4)-Kdo-(2→4)]-Kdo is found in nature as a partial structure of E. coli LPS. The premature end of the biosynthesis and incorporation of Hep into the LPS indicated that WaaC had access to the substrate before Kdo transfer was completed. We have observed differences between WaaA of C. trachomatis, C. pneumoniae and C. psittaci which indicate mechanistic differences between these Kdo transferases
biosynthesis, LPS, Escherichia coli, Kdo, Hep, WaaA, WaaC, WaaF, Chlamydiae
NCBI PubMed ID: 19201821Journal NLM ID: 101469670Publisher: Sage Publications
Correspondence: sml@fz-borstel.de
Institutions: Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany
Methods: 13C NMR, 1H NMR, SDS-PAGE, 31P NMR, ESI-MS, ESI-FTICR-MS, Western blotting, composition analysis, genetic methods
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5. Compound ID: 6573
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L-gro-a-D-manHepp-(1-6)-+ EtN-(1---P---P---4)-+ EtN-(1--P--7)--Kdop-(2-4)-+
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D-Glcp-(1-3)-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/lipid A/
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P-4)-+
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_140088,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150756,IEDB_153543,IEDB_153755,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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6. Compound ID: 6574
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EtN-(1--P--7)--Kdop-(2-4)-+
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L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_140088,IEDB_150756,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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7. Compound ID: 6575
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L-gro-D-manHepp-(1-6)-L-gro-D-manHepp-(1-3)-+ EtN-(1--P--7)--Kdop-(2-4)-+
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EtN-(1---P---P---4)-L-gro-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_140088,IEDB_150756,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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8. Compound ID: 6576
|
/Variants 0/-+
|
EtN-(1--P--7)--Kdop-(2-4)-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_150756
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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9. Compound ID: 6577
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EtN-(1--P--7)--Kdop-(2-4)-+
|
D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_140088,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150756,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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10. Compound ID: 6578
|
L-gro-a-D-manHepp-(1-5)-/Variants 0/-+
|
EtN-(1--P--7)--Kdop-(2-4)-Kdop-(2--/(2->?)lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
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Structure type: oligomer
Aglycon: (2->?)lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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11. Compound ID: 6580
|
EtN-(1--P--7)--Kdop-(2-4)-+
|
EtN-(1---P---P---4)-L-gro-a-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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12. Compound ID: 6581
|
L-gro-a-D-manHepp-(1-3)-+ EtN-(1--P--7)--Kdop-(2-4)-+
| |
EtN-(1---P---P---4)-L-gro-a-D-manHepp-(1-5)-/Variants 0/-Kdop-(2--/(2->?) lipid A/
/Variants 0/ is:
Kdop-(2-8)-
OR (exclusively)
Kdop-(2-7)- |
Show graphically |
Structure type: oligomer
Aglycon: (2->?) lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130658,IEDB_130659,IEDB_140088,IEDB_150756,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 2346
Prehm P, Stirm S, Jann B, Jann K "Cell-wall lipopolysaccharide from Escherichia coli B" -
European Journal of Biochemistry 56 (1975) 41-55
The lipopolysaccharide of Escherichia coli BB and a number of R-phage selected (e.g. T3, T4) cell-wall-defective mutants were analyzed. From their lipopolysaccharides the respective core oligosaccharides were obtained. Following dephosphorylation, the oligosaccharides were methylated and analyzed by gas chromatography/mass spectrometry. This revealed the sugar sequence in the hexose-heptose region of the core. The linkage of heptose (Hep) to 2-keto-3-deoxyoctonate (KDO) was established as ... Hep 1,5→KDO ... by methylation analysis. The substituted derivative of KDO was identified by gas chromatography and mass spectrometry. The KDO region contains three KDO units. Its structure was elaborated by (a) selective removal and identification of 7-phosphoryl ethanolamine-KDO (KDO-PN), (b) periodate oxidation and thiobarbituric acid reaction in conjunction with mild hydrolysis, (c) a modified methylation analysis. Phosphate substitution of E. coli BB core was studied by beta-elimination and using the information obtained with KDO-PN. The structures of the cell wall lipopolysaccharides from E. coli BB and cell-wall-defective mutants are given.
NCBI PubMed ID: 1100390Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: GC-MS
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13. Compound ID: 6926
Structure type: oligomer
Aglycon: lipid A
Trivial name: Kdo region of LPS
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_150901,IEDB_151769
The structure is contained in the following publication(s):
- Article ID: 3163
Müller-Loennies S, Gronow S, Brade L, Mackenzie R, Kosma P, Brade H "A monoclonal antibody against a carbohydrate epitope in lipopolysaccharide differentiates Chlamydophila psittaci from Chlamydophila pecorum, Chlamydophila pneumoniae, and Chlamydia trachomatis" -
Glycobiology 16(3) (2006) 184-196
Lipopolysaccharide (LPS) of Chlamydophila psittaci but not of Chlamydophila pneumoniae or Chlamydia trachomatis contains a tetrasaccharide of 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (Kdo) of the sequence Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo. After immunization with the synthetic neoglycoconjugate antigen Kdo(2→8)[Kdo(2→4)]Kdo(2→4) Kdo-BSA, we obtained the mouse monoclonal antibody (mAb) S69-4 which was able to differentiate C. psittaci from Chlamydophila pecorum, C. pneumoniae, and C. trachomatis in double labeling experiments of infected cell monolayers and by enzyme-linked immunosorbent assay (ELISA). The epitope specificity of mAb S69-4 was determined by binding and inhibition assays using bacteria, LPS, and natural or synthetic Kdo oligosaccharides as free ligands or conjugated to BSA. The mAb bound preferentially Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo(2→4) with a K(d) of 10 microM, as determined by surface plasmon resonance (SPR) for the monovalent interaction using mAb or single chain Fv. Cross-reactivity was observed with Kdo(2→4)Kdo(2→4)Kdo but not with Kdo(2→8)Kdo(2→4)Kdo, Kdo disaccharides in 2→4- or 2→8-linkage, or Kdo monosaccharide. MAb S69-4 was able to detect LPS on thin-layer chromatography (TLC) plates in amounts of <10 ng by immunostaining. Due to the high sensitivity achieved in this assay, the antibody also detected in vitro products of cloned Kdo transferases of Chlamydia. The antibody can therefore be used in medical and veterinarian diagnostics, general microbiology, analytical biochemistry, and studies of chlamydial LPS biosynthesis. Further contribution to the general understanding of carbohydrate-binding antibodies was obtained by a comparison of the primary structure of mAb S69-4 to that of mAb S45-18 of which the crystal structure in complex with its ligand has been elucidated recently (Nguyen et al., 2003, Nat. Struct. Biol., 10, 1019-1025).
Kdo, diagnostic, neoglycoconjugate, immunofluorescence
NCBI PubMed ID: 16282606Publication DOI: 10.1093/glycob/cwj055Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: hebra@fz-borstel.de
Institutions: Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Institute for Biological Sci-ences, National Research Council Canada, Ottawa, Ontario, Canada K1A 0R6, Department of Chemistry, University of Natural Resources and Applied Life Sciences, A-1190 Vienna, Austri
Methods: serological methods, genetic methods
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14. Compound ID: 6932
|
a-Kdop-(2-8)-+
|
a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2--/OCH2CH=CH2 or BSA/ |
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Structure type: oligomer
Aglycon: OCH2CH=CH2 or BSA
Trivial name: neoglycoconjugate
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_150756,IEDB_150901,IEDB_151769
The structure is contained in the following publication(s):
- Article ID: 3163
Müller-Loennies S, Gronow S, Brade L, Mackenzie R, Kosma P, Brade H "A monoclonal antibody against a carbohydrate epitope in lipopolysaccharide differentiates Chlamydophila psittaci from Chlamydophila pecorum, Chlamydophila pneumoniae, and Chlamydia trachomatis" -
Glycobiology 16(3) (2006) 184-196
Lipopolysaccharide (LPS) of Chlamydophila psittaci but not of Chlamydophila pneumoniae or Chlamydia trachomatis contains a tetrasaccharide of 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (Kdo) of the sequence Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo. After immunization with the synthetic neoglycoconjugate antigen Kdo(2→8)[Kdo(2→4)]Kdo(2→4) Kdo-BSA, we obtained the mouse monoclonal antibody (mAb) S69-4 which was able to differentiate C. psittaci from Chlamydophila pecorum, C. pneumoniae, and C. trachomatis in double labeling experiments of infected cell monolayers and by enzyme-linked immunosorbent assay (ELISA). The epitope specificity of mAb S69-4 was determined by binding and inhibition assays using bacteria, LPS, and natural or synthetic Kdo oligosaccharides as free ligands or conjugated to BSA. The mAb bound preferentially Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo(2→4) with a K(d) of 10 microM, as determined by surface plasmon resonance (SPR) for the monovalent interaction using mAb or single chain Fv. Cross-reactivity was observed with Kdo(2→4)Kdo(2→4)Kdo but not with Kdo(2→8)Kdo(2→4)Kdo, Kdo disaccharides in 2→4- or 2→8-linkage, or Kdo monosaccharide. MAb S69-4 was able to detect LPS on thin-layer chromatography (TLC) plates in amounts of <10 ng by immunostaining. Due to the high sensitivity achieved in this assay, the antibody also detected in vitro products of cloned Kdo transferases of Chlamydia. The antibody can therefore be used in medical and veterinarian diagnostics, general microbiology, analytical biochemistry, and studies of chlamydial LPS biosynthesis. Further contribution to the general understanding of carbohydrate-binding antibodies was obtained by a comparison of the primary structure of mAb S69-4 to that of mAb S45-18 of which the crystal structure in complex with its ligand has been elucidated recently (Nguyen et al., 2003, Nat. Struct. Biol., 10, 1019-1025).
Kdo, diagnostic, neoglycoconjugate, immunofluorescence
NCBI PubMed ID: 16282606Publication DOI: 10.1093/glycob/cwj055Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: hebra@fz-borstel.de
Institutions: Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Institute for Biological Sci-ences, National Research Council Canada, Ottawa, Ontario, Canada K1A 0R6, Department of Chemistry, University of Natural Resources and Applied Life Sciences, A-1190 Vienna, Austri
Methods: serological methods, genetic methods
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15. Compound ID: 6933
|
a-Kdop-(2-8)-+ P-4)-+
| |
a-Kdop-(2-4)-a-Kdop-(2-4)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-a-D-GlcpNAc-(1---P---/BSA/ |
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Structure type: oligomer
Aglycon: BSA
Trivial name: neoglycoconjugate
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_130662,IEDB_135394,IEDB_135813,IEDB_137340,IEDB_140092,IEDB_141807,IEDB_150077,IEDB_150755,IEDB_150756,IEDB_150760,IEDB_150901,IEDB_150908,IEDB_151531,IEDB_151767,IEDB_151768,IEDB_151769,IEDB_156486,IEDB_156487,IEDB_164045
The structure is contained in the following publication(s):
- Article ID: 3163
Müller-Loennies S, Gronow S, Brade L, Mackenzie R, Kosma P, Brade H "A monoclonal antibody against a carbohydrate epitope in lipopolysaccharide differentiates Chlamydophila psittaci from Chlamydophila pecorum, Chlamydophila pneumoniae, and Chlamydia trachomatis" -
Glycobiology 16(3) (2006) 184-196
Lipopolysaccharide (LPS) of Chlamydophila psittaci but not of Chlamydophila pneumoniae or Chlamydia trachomatis contains a tetrasaccharide of 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (Kdo) of the sequence Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo. After immunization with the synthetic neoglycoconjugate antigen Kdo(2→8)[Kdo(2→4)]Kdo(2→4) Kdo-BSA, we obtained the mouse monoclonal antibody (mAb) S69-4 which was able to differentiate C. psittaci from Chlamydophila pecorum, C. pneumoniae, and C. trachomatis in double labeling experiments of infected cell monolayers and by enzyme-linked immunosorbent assay (ELISA). The epitope specificity of mAb S69-4 was determined by binding and inhibition assays using bacteria, LPS, and natural or synthetic Kdo oligosaccharides as free ligands or conjugated to BSA. The mAb bound preferentially Kdo(2→8)[Kdo(2→4)]Kdo(2→4)Kdo(2→4) with a K(d) of 10 microM, as determined by surface plasmon resonance (SPR) for the monovalent interaction using mAb or single chain Fv. Cross-reactivity was observed with Kdo(2→4)Kdo(2→4)Kdo but not with Kdo(2→8)Kdo(2→4)Kdo, Kdo disaccharides in 2→4- or 2→8-linkage, or Kdo monosaccharide. MAb S69-4 was able to detect LPS on thin-layer chromatography (TLC) plates in amounts of <10 ng by immunostaining. Due to the high sensitivity achieved in this assay, the antibody also detected in vitro products of cloned Kdo transferases of Chlamydia. The antibody can therefore be used in medical and veterinarian diagnostics, general microbiology, analytical biochemistry, and studies of chlamydial LPS biosynthesis. Further contribution to the general understanding of carbohydrate-binding antibodies was obtained by a comparison of the primary structure of mAb S69-4 to that of mAb S45-18 of which the crystal structure in complex with its ligand has been elucidated recently (Nguyen et al., 2003, Nat. Struct. Biol., 10, 1019-1025).
Kdo, diagnostic, neoglycoconjugate, immunofluorescence
NCBI PubMed ID: 16282606Publication DOI: 10.1093/glycob/cwj055Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: hebra@fz-borstel.de
Institutions: Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Institute for Biological Sci-ences, National Research Council Canada, Ottawa, Ontario, Canada K1A 0R6, Department of Chemistry, University of Natural Resources and Applied Life Sciences, A-1190 Vienna, Austri
Methods: serological methods, genetic methods
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