Found 182 structures.
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1. Compound ID: 86
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Subst-(1-5)-+
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a-Kdop-(2-4)-a-Ko-(2--/lipid A/
Subst = core oligosaccharide;
Ko = D-glycero-a-D-talo-oct-2-ulosonic acid |
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Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: IEDB_130650,IEDB_135608,IEDB_135609
The structure is contained in the following publication(s):
- Article ID: 17
Bode CE, Brabetz W, Brade H "Cloning and characterization of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferase genes (kdtA) from Acinetobacter baumannii and Acinetobacter haemolyticus" -
European Journal of Biochemistry 254(2) (1998) 404-412
3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferases (KdtA) are multifunctional glycosyltransferases with primary structures of low similarity. Totally degenerated primers were deduced from two stretches of identical amino acids between known KdtA sequences and used to amplify by PCR a kdtA-specific fragment from Acinetobacter baumannii ATCC 15308 DNA which was then applied as a probe for the cloning and sequencing of the complete Kdo transferase gene. With conserved PCR primers for this structural gene from A. baumannii ATCC 15308, also kdtA genes of A. baumannii ATCC 19606 and A. haemolyticus ATCC 17906 were obtained, cloned from the chromosome and sequenced. The genes coded for proteins with similarities to known Kdo transferases. Within the genus Acinetobacter, the identity and similarity of the deduced amino acid sequences were 71% and 84.5%, respectively. The kdtA sequences of both A. baumannii strains were identical and possessed a TTG start codon, whereas ATG was found in the case of A. haemolyticus. The genes from Acinetobacter and kdtA from Escherichia coli K-12 were expressed in the Gram-positive bacterium Corynebacterium glutamicum. In vitro tests confirmed the function of the gene products as Kdo transferases, which transferred mainly two Kdo residues to a synthetic lipid A precursor of E. coli. Also, no differences between the cloned kdtA genes from A. baumanniii, A. haemnolyticus and E. coli were observed when tetraacyl or hexaacyl lipid A were tested, since all transferases acted more efficiently on the former. With limiting amounts of acceptor, all Kdo transferases were able to transfer a third Kdo residue with varying efficiency
gene, characterization, 3-deoxy-D-manno-oct-2-ulosonic acid, acid, Acinetobacter, Acinetobacter baumannii, Acinetobacter haemolyticus, cloning, Kdo, lipopolysaccharide biosynthesis, shuttle plasmid, transferase
NCBI PubMed ID: 9660198Publication DOI: 10.1046/j.1432-1327.1998.2540404.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: hbrade@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
Methods: PCR, DNA sequencing, DNA cloning
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2. Compound ID: 174
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b-D-GlcpNAc-(1-3)-+ b-D-Glcp-(1-4)-+ /Variants 0/-+
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b-D-Galp-(1-7)-L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
a-Kop-(2-4)-
OR (exclusively)
a-Kdop-(2-4)- |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- 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: 14670707Publication DOI: 10.1016/j.carres.2003.07.010Journal NLM ID: 0043535Publisher: 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
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3. Compound ID: 690
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?%L-Arap4N-(1--P--1)--+
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?%L-Arap4N-(1--P--4)--+ |
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L-gro-a-D-manHepp-(1-7)-+ b-D-Glcp-(1-4)-+ a-Kop-(2-4)-+ | |
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L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_137340,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 185
Vinogradov E, Lindner B, Seltmann G, Radziejewska-Lebrecht J, Holst O "The structures of the core-lipid A regions of lipopolysaccharides from Serratia marcescens" -
Proceedings of International Carbohydrate Symposium (21st : 2002 : Cairns, Queensland) (2002) 279
Lipopolysaccharide, lipopolysaccharides, structure, core, carbohydrate, Serratia marcescens, region, core-lipid A region, Serratia, structue
Institutions: Institute for Biological Sciences, NRCC, 100 Sussex Dr., Ottawa, ON K1A 0R6, Canada, Division of Biophysics, Research Center Borstel, Parkallee 10, D-23845 Borstel, Germany, Robert-Koch-Institute, Burgstr. 37, D-38855 Wernigerode, Germany, Institute of Microbiology, Silesian University, Jagiellonska 28, PL-40-032 Katowice, Poland, Division of Structural Biochemistry, Research Center Borstel, Borstel, Germany
Methods: NMR, chemical analysis, mild acid hydrolysis, deamination, de-O-acylation with hydrazine, alkaline deacylation
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4. Compound ID: 692
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?%L-Arap4N-(1--P--1)--+
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?%L-Arap4N-(1--P--4)--+ |
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L-gro-a-D-manHepp-(1-7)-+ | |
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L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-+ | b-D-Glcp-(1-4)-+ L-Arap4N-(1-8)-+ | |
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b-D-Glcp-(1-6)-a-D-Glcp-(1-4)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN
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a-Kop-(2-4)-+ |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_137340,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141806,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 185
Vinogradov E, Lindner B, Seltmann G, Radziejewska-Lebrecht J, Holst O "The structures of the core-lipid A regions of lipopolysaccharides from Serratia marcescens" -
Proceedings of International Carbohydrate Symposium (21st : 2002 : Cairns, Queensland) (2002) 279
Lipopolysaccharide, lipopolysaccharides, structure, core, carbohydrate, Serratia marcescens, region, core-lipid A region, Serratia, structue
Institutions: Institute for Biological Sciences, NRCC, 100 Sussex Dr., Ottawa, ON K1A 0R6, Canada, Division of Biophysics, Research Center Borstel, Parkallee 10, D-23845 Borstel, Germany, Robert-Koch-Institute, Burgstr. 37, D-38855 Wernigerode, Germany, Institute of Microbiology, Silesian University, Jagiellonska 28, PL-40-032 Katowice, Poland, Division of Structural Biochemistry, Research Center Borstel, Borstel, Germany
Methods: NMR, chemical analysis, mild acid hydrolysis, deamination, de-O-acylation with hydrazine, alkaline deacylation
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5. Compound ID: 693
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?%L-Arap4N-(1--P--1)--+
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?%L-Arap4N-(1--P--4)--+ |
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L-gro-a-D-manHepp-(1-7)-+ b-D-Glcp-(1-4)-+ L-Arap4N-(1-8)-+ | |
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L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN
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a-Kop-(2-4)-+ |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_137340,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 185
Vinogradov E, Lindner B, Seltmann G, Radziejewska-Lebrecht J, Holst O "The structures of the core-lipid A regions of lipopolysaccharides from Serratia marcescens" -
Proceedings of International Carbohydrate Symposium (21st : 2002 : Cairns, Queensland) (2002) 279
Lipopolysaccharide, lipopolysaccharides, structure, core, carbohydrate, Serratia marcescens, region, core-lipid A region, Serratia, structue
Institutions: Institute for Biological Sciences, NRCC, 100 Sussex Dr., Ottawa, ON K1A 0R6, Canada, Division of Biophysics, Research Center Borstel, Parkallee 10, D-23845 Borstel, Germany, Robert-Koch-Institute, Burgstr. 37, D-38855 Wernigerode, Germany, Institute of Microbiology, Silesian University, Jagiellonska 28, PL-40-032 Katowice, Poland, Division of Structural Biochemistry, Research Center Borstel, Borstel, Germany
Methods: NMR, chemical analysis, mild acid hydrolysis, deamination, de-O-acylation with hydrazine, alkaline deacylation
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6. Compound ID: 718
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L-gro-a-D-manHepp-(1-7)-+
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L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-+ | b-D-Glcp-(1-4)-+ a-Kop-(2-4)-+
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b-D-Glcp-(1-6)-a-D-Glcp-(1-4)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141806,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 190
Vinogradov E, Petersen BO, Duus JO, Radziejewska-Lebrecht J "The structure of the polysaccharide part of the LPS from Serratia marcescens serotype O19, including linkage region to the core and the residue at the non-reducing end" -
Carbohydrate Research 338(23) (2003) 2757-2761
The structure of the LPS from Serratia marcescens serotype O19 was investigated. Deamination of the LPS released the O-chain polysaccharide together with a fragment of the core oligosaccharide. The following structure of the product was determined by NMR spectroscopy, mass spectrometry, and chemical methods: [carbohydrate structure: see text] The main polymer consists of a repeating disaccharide V-U and is present on average of 18 units per chain as estimated by integration of signals in the NMR spectra. The residue O corresponds to the primer, which initiates biosynthesis of the O-chain, and an oligomer of a disaccharide R-S is an insert between the primer and the main polymer. The polysaccharide has a β-Kdo residue at the non-reducing end, a feature similar to that observed previously in the LPS from Klebsiella O12.
LPS, structure, core, polysaccharide, serotype, linkage, Serratia marcescens, region, nonreducing, Serratia
NCBI PubMed ID: 14670734Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Carlsberg Laboratory, Department of Chemistry, Gamle Carlsberg Vej 10, DK-2500 Valby, Copenhagen, Denmark, Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6, Uniwersytet Slaski, Katedra Mikrobiologii, ul. Jagiellonska 28, 40-032 Katowice, Poland
Methods: NMR-2D, NMR, chemical methods, MS
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7. Compound ID: 735
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
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a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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8. Compound ID: 737
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a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-D-GlcN-ol |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_135609,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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9. Compound ID: 739
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a-Kdop-(2-4)-+ P-4)-+
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a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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10. Compound ID: 741
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
| | |
a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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11. Compound ID: 742
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-D-Glc-ol |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_114708,IEDB_135609,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 195
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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12. Compound ID: 744
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a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-+ P-4)-+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-7)-a-Kdop-(2-4)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 196
Vinogradov EV, Bock K, Petersen BO, Holst O, Brade H "The structure of the carbohydrate backbone of the lipopolysaccharide from Acinetobacter strain ATCC 17905" -
European Journal of Biochemistry 243(1-2) (1997) 122-127
The structure of the carbohydrate backbone of the lipopolysaccharide from Acinetobacter strain ATCC 17905 was studied. After deacylation of the lipopolysaccharide, a mixture of two compounds (ratio approximately 2:1) was isolated by high-performance anion-exchange chromatography, the structures of which were determined by NMR spectroscopy and electrospray-mass spectrometry as: [see formula in text] [Sug, 3-deoxy-D-manno-2-octulopyranosonic acid (Kdo) in oligosaccharide 1 (major portion) and D-glycero-D-talo-2-octulopyranosonic acid (Ko) in oligosaccharide 2 (minor portion)]. All monosaccharide residues also possess th D-cofiguration and are present in the pyranose form.
Lipopolysaccharide, NMR, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9030730Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Biochemical Microbiology, Center for Medicine und Biosciences, Research Center Borstel, Germany
Methods: NMR-2D, NMR, ESI-MS
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13. Compound ID: 776
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b-D-GlcpNAc-(1-3)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
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b-D-Galp-(1-7)-L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135608,IEDB_135609,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 201
Vinogradov EV, Lindner B, Kocharova NA, Senchenkova SN, Shashkov AS, Knirel YA, Holst O, Gremyakova TA, Shaikhutdinova RZ, Anisimov AP "The core structure of the lipopolysaccharide from the causative agent o plague, Yersinia pestis" -
Carbohydrate Research 337 (2002) 755-777
The rough-type lipopolysaccharide (LPS) of the plague pathogen, Yersinia pestis, was studied afer mild-acid and strong-alkaline degradations by chemical analyses, NmR spectroscopy and eslectrospray-ionization mass spectrometry, and the following structure of the core region was determined: [see formula in text] where L-a-D-Hep stands for L-glycero-a-D-manno-heptose, Sug1 for either 3-deoxy-a-D-manno-oct-2-ulosonic acid (a-Kdo) ore D-glycero-a-D-talo-oct-2-ulosonic acid (a-Ko), and Sug2 for either b-D-galactose or D-glycero-a-D-manno-heptose. A minority of the LPS molecules lacks GlcNAc
Lipopolysaccharide, core structure, ersinia pestis
NCBI PubMed ID: 11856300Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, N.L. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Centre for Applied Microgiology, Obolensk, Moscow Region 142279, Russia, N.L. Zelinskty Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR-2D, NMR, chemical analysis, ESI-MS
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14. Compound ID: 778
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b-D-GlcpNAc-(1-3)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
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D-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135608,IEDB_135609,IEDB_135813,IEDB_137340,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189046,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 201
Vinogradov EV, Lindner B, Kocharova NA, Senchenkova SN, Shashkov AS, Knirel YA, Holst O, Gremyakova TA, Shaikhutdinova RZ, Anisimov AP "The core structure of the lipopolysaccharide from the causative agent o plague, Yersinia pestis" -
Carbohydrate Research 337 (2002) 755-777
The rough-type lipopolysaccharide (LPS) of the plague pathogen, Yersinia pestis, was studied afer mild-acid and strong-alkaline degradations by chemical analyses, NmR spectroscopy and eslectrospray-ionization mass spectrometry, and the following structure of the core region was determined: [see formula in text] where L-a-D-Hep stands for L-glycero-a-D-manno-heptose, Sug1 for either 3-deoxy-a-D-manno-oct-2-ulosonic acid (a-Kdo) ore D-glycero-a-D-talo-oct-2-ulosonic acid (a-Ko), and Sug2 for either b-D-galactose or D-glycero-a-D-manno-heptose. A minority of the LPS molecules lacks GlcNAc
Lipopolysaccharide, core structure, ersinia pestis
NCBI PubMed ID: 11856300Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, N.L. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Centre for Applied Microgiology, Obolensk, Moscow Region 142279, Russia, N.L. Zelinskty Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR-2D, NMR, chemical analysis, ESI-MS
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15. Compound ID: 814
Structure type: monomer
Contained glycoepitopes: IEDB_135609
The structure is contained in the following publication(s):
- Article ID: 219
Wimmer N, Brade H, Kosma P "Synthesis of neoglycoproteins containing D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko) ligands corresponding to core units from Burkholderia and Acinetobacter lipopolysaccharide" -
Carbohydrate Research 329(3) (2000) 549-560
Glycal esters of Kdo derivatives were converted into 2,3-anhydro intermediates, which were transformed into D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko), as well as 3-O- and 4-O-p-nitrobenzoyl-Ko derivatives. The exo-allyl orthoester derivative, methyl {5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylidene]-Dglycero-b-D-talo-oct-2-ulopyranos}onate, prepared from the 4-O-pNBz-protected Ko derivative, was elaborated into the a-Ko allyl ketoside, the reducing disaccharide a-Kdop-(2→4)-Ko and the disaccharide a-Kdop-(2→4)-Kop-(2→OAll). Conversely, methyl[4,5,7,8-tetra-O-acetyl-3-O-(4-nitrobenzoyl)-a-D-glycero-D-talo-2-octulopyranosyl bromide] onate [Carbohydr. Res., 244 (1993) 69-84], was coupled with a Kdo acceptor to give the disaccharide a-Kop-(2→4)-Kdop-(2→OAll) after orthoester rearrangement and deprotection. The allyl glycosides were treated with cysteamine and converted into neoglycoproteins. The ligands correspond to inner core units from Acinetobacter haemolyticus and Burkholderia cepacia lipopolysaccharides.
Lipopolysaccharide, synthesis, core, Burkholderia, acid, Acinetobacter, epitope, epitopes, specific, Ko, ligand, Ligands, neoglycoprotein, neoglycoproteins
NCBI PubMed ID: 11128584Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: pkosma@edv2.boku.ac.at
Institutions: Institute of Chemistry, University of Agricultural Sciences, Muthgasse 18, A- 1190 Vienna, Austria, Research Center Borstel, D- 23845 Borstel, Germany
Methods: chemical methods
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