Show legend Show as text

Structure type: oligomer
Trivial name: glycoform 2 core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_1330403,IEDB_135394,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_189517,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 33
  Bystrova OV, Lindner B, Moll H, Kocharova NA, Knirel YA, Zähringer U, Pier GB "Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region" - Carbohydrate Research 338(18) (2003) 1895-1905
  

  The lipopolysaccharide of Pseudomonas aeruginosa O-12 was studied by strong alkaline and mild acid degradations and dephosphorylation followed by fractionation of the products by GPC and high-performance anion-exchange chromatography and analyses by ESI FT-MS and NMR spectroscopy. The structures of the lipopolysaccharide core and the O-polysaccharide repeating unit were elucidated and the site and the configuration of the linkage between the O-polysaccharide and the core established. The core was found to be randomly O-acetylated, most O-acetyl groups being located on the terminal rhamnose residue of the outer core region

  Lipopolysaccharide, Pseudomonas aeruginosa, core structures, O-antigen repeating unit, O-acetylation

  NCBI PubMed ID: 12932374
  Publication DOI: 10.1016/S0008-6215(03)00290-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, dephosphorylation, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation, HPAEC
  
   
  
  Pseudomonas aeruginosa O12
  CSDB ID 1823 (all data & tools)

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Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 33
  Bystrova OV, Lindner B, Moll H, Kocharova NA, Knirel YA, Zähringer U, Pier GB "Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region" - Carbohydrate Research 338(18) (2003) 1895-1905
  

  The lipopolysaccharide of Pseudomonas aeruginosa O-12 was studied by strong alkaline and mild acid degradations and dephosphorylation followed by fractionation of the products by GPC and high-performance anion-exchange chromatography and analyses by ESI FT-MS and NMR spectroscopy. The structures of the lipopolysaccharide core and the O-polysaccharide repeating unit were elucidated and the site and the configuration of the linkage between the O-polysaccharide and the core established. The core was found to be randomly O-acetylated, most O-acetyl groups being located on the terminal rhamnose residue of the outer core region

  Lipopolysaccharide, Pseudomonas aeruginosa, core structures, O-antigen repeating unit, O-acetylation

  NCBI PubMed ID: 12932374
  Publication DOI: 10.1016/S0008-6215(03)00290-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, dephosphorylation, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation, HPAEC
  
   
  
  Pseudomonas aeruginosa O12
  CSDB ID 1824 (all data & tools)
• Article ID: 3490
  King JD, Mulrooney EF, Vinogradov E, Kneidinger B, Mead K, Lam JS "lfnA from Pseudomonas aeruginosa O12 and wbuX from Escherichia coli O145 encode membrane-associated proteins and are required for expression of 2,6-dideoxy-2-acetamidino-L-galactose in lipopolysaccharide O antigen" - Journal of Bacteriology 190(5) (2008) 1671-1679
  

  The rare sugar 2,6-dideoxy-2-acetamidino-L-galactose (L-FucNAm) is found only in bacteria and is a component of cell surface glycans in a number of pathogenic species, including the O antigens of Pseudomonas aeruginosa serotype O12 and Escherichia coli O145. P. aeruginosa is an important opportunistic pathogen, and the O12 serotype is associated with multidrug-resistant epidemic outbreaks. O145 is one of the classic non-O157 serotypes associated with Shiga toxin-producing, enterohemorrhagic E. coli. The acetamidino (NAm) moiety of L-FucNAm is of interest, because at neutral pH it contributes a positive charge to the cell surface, and we aimed to characterize the biosynthesis of this functional group. The pathway is not known, but expression of NAm-modified sugars coincides with the presence of a pseA homologue in the relevant biosynthetic locus. PseA is a putative amidotransferase required for synthesis of a NAm-modified sugar in Campylobacter jejuni. In P. aeruginosa O12 and E. coli O145, the pseA homologues are lfnA and wbuX, respectively, and we hypothesized that these genes function in L-FucNAm biosynthesis. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis, Western blotting, and nuclear magnetic resonance analysis of the lfnA mutant O-antigen structure indicated that the mutant expresses 2,6-dideoxy-2-acetamido-L-galactose (L-FucNAc) in place of L-FucNAm. The mutation could be complemented by expression of either His(6)-tagged lfnA or wbuX in trans, confirming that these genes are functional homologues and that they are required for NAm moiety synthesis. Both proteins retained their activity when fused to a His(6) tag and localized to the membrane fraction. These data will assist future biochemical investigation of this pathway.

  biosynthesis, O-antigen, Pseudomonas aeruginosa, Membrane Proteins, lfnA, wbuX

  NCBI PubMed ID: 18156256
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, mild acid hydrolysis, Western blotting, genetic methods
  
   
  
  Pseudomonas aeruginosa O12
  CSDB ID 23007 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137777,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 52
  Edebrink P, Jansson P, Bogwald J, Hoffman J "Structural studies of the Vibrio salmonicida lipopolysaccharide" - Carbohydrate Research 287 (1996) 225-245
  

  The oligosaccharide part of the Vibrio salmonicida (strain NCMB 2262) lipopolysaccharide was isolated by mild acid hydrolysis followed by gel-permeation chromatography. The structure was established mainly by methylation analysis, mass spectrometry, and NMR spectroscopy. It is concluded that the oligosaccharide has the following structure, in which L-α-D-Hepp is L-glycero-α-D-manno-heptopyranose, D-α-D-Hepp is D-glycero-α-D-manno-heptopyranose, α-D-Fucp4N is 4-amino-4,6-dideoxy-α-D-galactopyranose, α-NonA is 5-acetamidino-7-acetamido-3,5,7, 9-tetradeoxy-L-glycero-α-D-galacto-nonulosonic acid, BA is (R)-3-hydroxybutanoyl, and PEA is phosphoethanolamine. The substitution pattern of the branching heptosyl residue was deduced from 1H NMR chemical shifts and conformations of the branching region, obtained by molecular modeling. The absolute configuration for NonA was determined by NMR spectroscopy from NOE correlations to the neighbouring sugar and 13C NMR chemical shift data. It could also be shown that assignments of nonulosonic acids with the D-glycero-L-galacto configuration, reported by previous investigators, are erroneous and should be changed to L-glycero-D-galacto. The oligosaccharide is assumed to be linked to the 5-position of a Kdo residue, phosphorylated in the 4-position as observed for other lipopolysaccharides from Vibrionaceae. [formula: see text]

  Lipopolysaccharide, NMR, structure, Salmon, nonulosonic acid

  NCBI PubMed ID: 8766209
  Publication DOI: 10.1016/0008-6215(96)00076-6
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Organic Chemistry, Stockholm University, Sweden, Clinical Research Centre, Analitycal Unit, Karolinska Institute, Huddinge, Sweden, Norwegian Institute of Fisheries and Aquaculture Ltd, Tromso, Norway
  Methods: methylation, NMR-2D, NMR, sugar analysis, MS
  
   
  
  Vibrio salmonicida
  CSDB ID 2029 (all data & tools)
• Article ID: 5195
  Norstebo SF, Lotherington L, Landsverk M, Bjelland AM, Sorum H "Aliivibrio salmonicida requires O-antigen for virulence in Atlantic salmon (Salmo salar L.)" - Microbial Pathogenesis 124 (2018) 322-331
  

  Aliivibrio salmonicida is the causative agent of cold-water vibriosis, a hemorrhagic septicemia of salmonid fish. The bacterium has been shown to rapidly enter the fish bloodstream, and proliferation in blood is seen after a period of latency. Although the pathogenesis of the disease is largely unknown, shedding of high quantities of outer-membrane complex VS-P1, consisting of LPS and a protein moiety, has been suggested to act as decoy and contribute to immunomodulation. To investigate the role of LPS in the pathogenesis, we constructed O-antigen deficient mutants by knocking out the gene encoding O-antigen ligase waaL. As this gene exists in two copies in the Al. salmonicida genome, we constructed single and double in-frame deletion mutants to explore potential effects of copy number variation. Our results demonstrate that the LPS structure of Al. salmonicida is essential for virulence in Atlantic salmon. As the loss of O-antigen did not influence invasive properties of the bacterium, the role of LPS in virulence applies to later stages of the pathogenesis. One copy of waaL was sufficient for O-antigen ligation and virulence in experimental models. However, as a non-significant decrease in mortality was observed after immersion challenge with a waaL single mutant, it is tempting to suggest that multiple copies of the gene are beneficial to the bacterium at lower challenge doses. The loss of O-antigen was not found to affect serum survival in vitro, but quantification of bacteria in blood following immersion challenge suggested a role in in vivo survival. Furthermore, fish challenged with the waaL double mutant induced a more transient immune response than fish challenged with the wild type strain. Whether the reduction in virulence following the loss of waaL is caused by altered immunomodulative properties or impaired survival remains unclear. However, our data demonstrate that LPS is crucial for development of disease.

  Lipopolysaccharide, Pathogenesis, O-antigen, Atlantic salmon, Aliivibrio salmonicida, Cold-water vibriosis

  NCBI PubMed ID: 30165113
  Publication DOI: 10.1016/j.micpath.2018.08.058
  Journal NLM ID: 8606191
  Publisher: Academic Press
  Correspondence: S.F. Norstebo
  Institutions: Department of Food Safety and Infection Biology, Faculty of Veterinary Medicine, Norwegian University of Life Sciences, PO Box 8146 Dep, 0033, Oslo, Norway, Department of Mechanical, Electronic and Chemical Engineering, Oslo and Akershus University College of Applied Sciences, PO Box 4 St. Olavs Plass, 0130, Oslo, Norway
  Methods: virulence assays, SDS-PAGE, DNA techniques, cytokine analysis, RT-PCR, RNA extraction
  
   
  
  Aliivibrio salmonicida NCMB 2262
  CSDB ID 12956 (all data & tools)

Show legend Show as text

Structure type: monomer

• Article ID: 124
  Tsvetkov YE, Shashkov AS, Knirel YA, Backinowsky LV, Zähringer U "Synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto- and -L-glycero-D-talo-nonulosonic acids, putative components of bacterial lipopolysaccharide" - Mendeleev Communications 10(3) (2000) 90-91
  

  The title acids were synthesised by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-guIose with oxalacetic acid and characterised by 1H and I3C NMR spectroscopy.

  Lipopolysaccharide, synthesis, LPS, 5, 7-diamino-3, 7, 9-teradeoxy-L-glycero-D-galacto-nonulosonic acid, 9-teradeoxy-L-glycero-D-talo-nonulosonic acid, Legionella pneumophila

  Publication DOI: 10.1070/MC2000v010n03ABEH001287
  Journal NLM ID: 9425965
  Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Forschungszentrum Borstel, Zentrum fiir Medizin und Biowissenschaften, 23845 Borstel, Germany
  Methods: 13C NMR, 1H NMR
  
   
  
  Legionella pneumophila
  CSDB ID 5237 (all data & tools)
• Article ID: 126
  Tsvetkov YE, Shashkov AS, Knirel YA, Zähringer U "Synthesis and NMR spectroscopy of nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids" - Carbohydrate Research 335(4) (2001) 221-243
  

  Derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids are essential constituents of some bacterial polysaccharides and glycoproteins. In order to establish reliably the configuration of the natural sugars, nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids were synthesized, including di-N-acetyl-legionaminic and -pseudaminic acids (the D-glycero-D-galacto and L-glycero-L-manno isomers, respectively) and their isomers at C-4, C-5, C-7, and C-8 having the L-glycero-D-galacto, D-glycero-D-talo, L-glycero-D-talo, D-glycero-L-altro, L-glycero-L-altro, D-glycero-L-manno, and L-glycero-L-gluco configurations. Synthesis was performed by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-gulose, -D-mannose, -D-talose, and -L-allose with oxalacetic acid under basic conditions, the reaction of the last two precursors being accompanied by epimerisation at C-2. The 1H and 13C NMR data of the synthetic compounds are discussed. Acetylated methyl esters of the C-7 and C-8 isomeric nonulosonic acids were prepared and used for analysis of the side-chain conformation by NMR spectroscopy.

  NMR, synthesis, LPS, Bacterial, acid, NMR spectroscopy, pseudaminic acid, putative, identification, spectroscopy, 5, 7-diamino-3, 7, 9-tetradeoxynon-2-ulosonic acid, lipopolysaccharide components, 7-diacetamido-3, 9-tetradeoxynon-2-ulosonic acids, 2, 4-diacetamido-2, 4, 6-trideoxyhexoses, legionaminic acid, 9-teradeoxynonulosonic acid, component, isomer

  NCBI PubMed ID: 11595217
  Publication DOI: 10.1016/S0008-6215(01)00235-X
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: tsvetkov@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russian Federation, Forschungszentrum Borstel, Zentrum fur Medizin und Biowissenschaften, Borstel, Germany.
  Methods: 13C NMR, 1H NMR
  
   
  
  (bacteria)
  CSDB ID 5350 (all data & tools)
• Article ID: 1231
  Shashkov AS, Torgov VI, Nazarenko EL, Zubkov VA, Gorshkova NM, Gorshkova RP, Widmalm G "Structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6" - Carbohydrate Research 337(12) (2002) 1119-1127
  

  The structure of the phenol-soluble polysaccharide from Shewanella putrefaciens strain A6 has been elucidated. Chemical modifications of the polymer in conjunction with 1H and 13C NMR spectroscopy, including 2D techniques, were employed in the analysis. It is concluded that the repeating unit is composed of two nine-carbon sugars as follows: →4)-α-NonpA-(2→3)-β-Sugp-(1→ where α-NonpA is 5-acetamido-7-acetamidino-8-O-acetyl-3,5,7,9-tetradeoxy-L-glycero-α-D-galacto-non-2-ulosonic acid (8eLeg) and β-Sugp is 2-acetamido-2,6-dideoxy-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-β-D-galactopyranose, with the proposed name Shewanellose (She).

  biosynthesis, polysaccharide, NMR spectroscopy, nonulosonic acid, shewanellose, Shewanella putrefaciens

  NCBI PubMed ID: 12062527
  Publication DOI: 10.1016/S0008-6215(02)00101-5
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: G. Widmalm
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation, Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, Stockholm, Sweden
  Methods: NMR
  
   
  
  Shewanella putrefaciens A6
  CSDB ID 4785 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137777,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 262
  Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" - Polish Journal of Chemistry 73 (1999) 1055-1067
  

  Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.

  Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence

  Journal NLM ID: 7901356
  WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055
  Publisher: Państwowe Wydawnictwo Naukowe
  Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
  
   
  
  Vibrio salmonicida NCMB 2262
  CSDB ID 31551 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,SB_74,SB_85

• Article ID: 381
  Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" - APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
  

  Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.

  Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics

  NCBI PubMed ID: 9048864
  Publication DOI: 10.1111/j.1699-0463.1996.tb04951.x
  Journal NLM ID: 8803400
  Publisher: Copenhagen: Munksgaard
  Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
  
   
  
  Yersinia ruckeri O1
  CSDB ID 31547 (all data & tools)
• Article ID: 2299
  Beynon LM, Richards JC, Perry MB "The structure of the lipopolysaccharide O antigen from Yersinia ruckeri serotype O1" - Carbohydrate Research 256 (1994) 303-317
  

  The O antigen obtained from the lipopolysaccharide of Yersinia ruckeri serotype 01, by mild acid hydrolysis, is composed of a branched tetrasaccharide repeating unit containing 2-acetamidino-2,6-dideoxy-l-galactose (l-FucAm), 2-acetamido-2-deoxy-d-glucose (D-GlcNac), and 7-acetamido-3,5,7,9-tetradeoxy-5-(4-hydroxybutyramido)-d-glycero-l-galacto-nonulosonic acid (l-Sug). Partial hydrolysis of the O antigen with 0.1 M HClafforded a trisaccharide and a tetrasaccharide having nonulosonic acid at their reducing ends. Cleavage of the O antigen with anhydrous methanolic hydrogen fluoride afforded the methyl glycoside derivatives of a trisaccharide and a tetrasaccharide. 1H and 13C NMR analysis, including 1H-13C heteronuclear multiple bond correlation spectroscopy to locate the N-acyl substituents, together with mass spectrometric analysis of the above oligosaccharides, allowed the structure of the O-specific polysaccharide to be assigned as: [formula: see text].

  NCBI PubMed ID: 7514497
  Publication DOI: 10.1016/0008-6215(94)84215-9
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
  
   
  
  Yersinia ruckeri O1
  CSDB ID 117883 (all data & tools)
• Article ID: 6301
  Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
  

  Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.

  chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal

  NCBI PubMed ID: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: J. Yin
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
  
   
  
  Yersinia ruckeri O1
  CSDB ID 9100 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 491 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 600 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 688
  Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O24 containing 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulosonic acid" - European Journal of Biochemistry 250 (1997) 617-623
  

  A polysaccharide containing D-GlcN, 2-amino-2,6-dideoxy-L-galactose (L-FucN), and 7-acetamido-5-acylamino-3,5,7,9-tetradeoxy-L-glycero-D-galacto-nonulo sonic acid (LegAX), in which the acyl group (X) is either S-3-hydroxybutyryl (50%) or acetyl (50%), was isolated by mild acid hydrolysis treatment, followed by gel-permeation chromatography, of the water-soluble lipopolysaccharide from Acinetobacter baumannii serogroup O24. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, methylation analysis and NMR studies, was shown to have a linear tetrasaccharide repeating unit, as depicted below. Serological tests indicated that the polymer corresponded to the O24 antigen. [→6)-α-D-GlcpNAc-(1→3)-α-L-FucpNAc-(1→3)-α-D-Glcp NAc-(1→4)-β-LegpAX-(1→].

  Lipopolysaccharide, O antigen, Acinetobacter baumannii, structural studies

  NCBI PubMed ID: 9428717
  Publication DOI: 10.1111/j.1432-1033.1997.0617a.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: School of Chemistry, University of Hull, England., School of Chemistry, University of Hull, England
  Methods: methylation, partial acid hydrolysis, NMR
  
   
  
  Acinetobacter baumannii O24
  CSDB ID 560 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide

• Article ID: 747
  Kilcoyne M, Shashkov AS, Senchenkova SN, Knirel YA, Vinogradov EV, Radziejewska-Lebrecht J, Galimska-Stypa R, Savage AV "Structural investigation of the O-specific polysaccharides of Morganella morganii consisting of two higher sugars" - Carbohydrate Research 337(18) (2002) 1697-1702
  

  The lipopolysaccharide of the bacterium Morganella morganii (strain KF 1676, RK 4222) yielded two polysaccharides, PS1 and PS2, when subjected to mild acid degradation followed by GPC. The polysaccharides were studied by 1H and 13C NMR spectroscopy, including two-dimensional COSY, TOCSY, NOESY, 1H,(13)C HMQC, and HMBC experiments. Each polysaccharide was found to contain a disaccharide repeating unit consisting of two higher sugars, 5-acetamidino-7-acetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic acid (a derivative of 8-epilegionaminic acid, 8eLeg5Am7Ac) and 2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-2,6-dideoxy-D-galactose (shewanellose, She). The two polysaccharides differ only in the ring size of shewanellose and have the following structures:Shewanellose has been previously identified in a phenol-soluble polysaccharide from Shewanella putrefaciens A6, which shows a close structural similarity to PS2.

  chemistry, structural, polysaccharide, carbohydrate, group, O-specific, O-specific polysaccharide, sugar, polysaccharides, 5, 7-diamino-3, 7, sugars, O-specific polysaccharides, higher sugar, Morganella, Morganella morganii, branched monosaccharide, 9-teradeoxy-L-glycero-D-galacto-non-2-ulosonic acid, shewanellose, 8-epilegionaminic acid

  NCBI PubMed ID: 12423973
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: angela.savage@nuigalway.ie
  Institutions: Department of Chemistry, National University of Ireland, Galway, Ireland
  Methods: NMR
  
   
  
  Morganella morganii KF1676, Morganella morganii RK4222
  CSDB ID 885 (all data & tools)
• Article ID: 1470
  Knirel YA, Shashkov AS, Tsvetkov YE, Jansson P, Zähringer U "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers: chemistry and biochemistry" - Book: Advances in Carbohydrate Chemistry and Biochemistry (2003) Vol. 58, 371-417
  

  This chapter provides an overview of the chemistry of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers. Ald-2-ulosonic acids are the important components of natural glycoconjugates. Sialic acids—namely, N- and O-acyl derivatives of 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid (neuraminic acid, Neu), generally occur in glycoconjugates of vertebrates and play a significant role in their recognition, regulation, and protection. A deamino analogue of neuraminic acid—3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn)—has also been found in a variety of animal tissues. 3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) is an essential component of lipopolysaccharides (LPSs) of Gram-negative bacteria that functions to link the carbohydrate portion to the lipid moiety. In rare cases, Kdo in LPS is replaced with a 3-hydroxylated analogue—D-glycero-D-talo-oct-2-ulosonic acid. The chapter focuses on the occurrence and characterization of derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids and presents experimental approaches that are used to identify them and to elucidate the structures of the bacterial polysaccharides that contain the nonulosonic acids. It also presents the recent data on the biosynthesis of these sugars and discusses their role in immune recognition.

  Lipopolysaccharide, LPS, structure, polysaccharide, Bacterial polysaccharide, 5, 7-diamino-3, 7, higher sugar, 9-tetradeoxynonulosonic acid

  NCBI PubMed ID: 14719362
  Publication DOI: 10.1016/S0065-2318(03)58007-6
  Publisher: Elsevier Inc.
  Correspondence: knirel@ioc.ac.ru
  Editors: Horton D
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  
   
  
  Morganella morganii KF 1676
  CSDB ID 31937 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Morganella morganii
  CSDB ID 27617 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide

• Article ID: 747
  Kilcoyne M, Shashkov AS, Senchenkova SN, Knirel YA, Vinogradov EV, Radziejewska-Lebrecht J, Galimska-Stypa R, Savage AV "Structural investigation of the O-specific polysaccharides of Morganella morganii consisting of two higher sugars" - Carbohydrate Research 337(18) (2002) 1697-1702
  

  The lipopolysaccharide of the bacterium Morganella morganii (strain KF 1676, RK 4222) yielded two polysaccharides, PS1 and PS2, when subjected to mild acid degradation followed by GPC. The polysaccharides were studied by 1H and 13C NMR spectroscopy, including two-dimensional COSY, TOCSY, NOESY, 1H,(13)C HMQC, and HMBC experiments. Each polysaccharide was found to contain a disaccharide repeating unit consisting of two higher sugars, 5-acetamidino-7-acetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic acid (a derivative of 8-epilegionaminic acid, 8eLeg5Am7Ac) and 2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-2,6-dideoxy-D-galactose (shewanellose, She). The two polysaccharides differ only in the ring size of shewanellose and have the following structures:Shewanellose has been previously identified in a phenol-soluble polysaccharide from Shewanella putrefaciens A6, which shows a close structural similarity to PS2.

  chemistry, structural, polysaccharide, carbohydrate, group, O-specific, O-specific polysaccharide, sugar, polysaccharides, 5, 7-diamino-3, 7, sugars, O-specific polysaccharides, higher sugar, Morganella, Morganella morganii, branched monosaccharide, 9-teradeoxy-L-glycero-D-galacto-non-2-ulosonic acid, shewanellose, 8-epilegionaminic acid

  NCBI PubMed ID: 12423973
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: angela.savage@nuigalway.ie
  Institutions: Department of Chemistry, National University of Ireland, Galway, Ireland
  Methods: NMR
  
   
  
  Morganella morganii KF1676, Morganella morganii RK4222
  CSDB ID 917 (all data & tools)
• Article ID: 1470
  Knirel YA, Shashkov AS, Tsvetkov YE, Jansson P, Zähringer U "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers: chemistry and biochemistry" - Book: Advances in Carbohydrate Chemistry and Biochemistry (2003) Vol. 58, 371-417
  

  This chapter provides an overview of the chemistry of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers. Ald-2-ulosonic acids are the important components of natural glycoconjugates. Sialic acids—namely, N- and O-acyl derivatives of 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid (neuraminic acid, Neu), generally occur in glycoconjugates of vertebrates and play a significant role in their recognition, regulation, and protection. A deamino analogue of neuraminic acid—3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn)—has also been found in a variety of animal tissues. 3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) is an essential component of lipopolysaccharides (LPSs) of Gram-negative bacteria that functions to link the carbohydrate portion to the lipid moiety. In rare cases, Kdo in LPS is replaced with a 3-hydroxylated analogue—D-glycero-D-talo-oct-2-ulosonic acid. The chapter focuses on the occurrence and characterization of derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids and presents experimental approaches that are used to identify them and to elucidate the structures of the bacterial polysaccharides that contain the nonulosonic acids. It also presents the recent data on the biosynthesis of these sugars and discusses their role in immune recognition.

  Lipopolysaccharide, LPS, structure, polysaccharide, Bacterial polysaccharide, 5, 7-diamino-3, 7, higher sugar, 9-tetradeoxynonulosonic acid

  NCBI PubMed ID: 14719362
  Publication DOI: 10.1016/S0065-2318(03)58007-6
  Publisher: Elsevier Inc.
  Correspondence: knirel@ioc.ac.ru
  Editors: Horton D
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  
   
  
  Morganella morganii KF 1676
  CSDB ID 31938 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Morganella morganii
  CSDB ID 27616 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192

• Article ID: 851
  Knirel YA, Helbig JH, Zähringer U "Structure of a decasaccharide isolated by mild acid degradation and dephosphorylation of the lipopolysaccharide of Pseudomonas fluorescens strain ATCC49271" - Carbohydrate Research 283 (1996) 129-139
  

  Mild acid degradation of the Pseudomonas fluorescens strain ATCC49271 lipopolysaccharide resulted in a core oligosaccharide containing D-glucose, 2-acetamido-2-deoxy-D-glucose, 2-(L- alanylamino)-2-deoxy-D-galactose, 2-acetamido-2,6-dideoxy-D-glucose (QuiNAc), 2-acetamido- 2,6-dideoxy-L-galactose (FucNAc), L-glycero-D-manno-heptose (Hep), 3-deoxy-D-manno-octulosonic acid (Kdo, present in multiple forms), and 5-acetamidino-7-acetamido-3,5,7,9- tetradeoxy- L-glycero-D-galacto-nonulosonic acid (a di-N-acyl derivative of legionaminic acid, Non) as well as O-acetyl, O-carbamoyl, and phosphate groups, including triphosphate groups. The dephosphorylated (HF) decasaccharide and products of its partial and full O-deacylation were studied by methylation analysis, GLC-MS, and 1H NMR spectroscopy, including 1D NOE and 2D shift-correlated spectroscopy (COSY). The core oligosaccharide of P. fluorescens strain ATCC49271 was found to be a decasaccharide (with partially degraded Kdo region) and one O-antigen repeating unit (di-N-acyllegionaminic acid, Non) attached. The following structure of the dephosphorylated core oligosaccharide was established: [sequence: see text]

  Lipopolysaccharide, structure, Pseudomonas, NMR spectroscopy, Pseudomonas fluorescens, core oligosacharide

  NCBI PubMed ID: 8901267
  Publication DOI: 10.1016/0008-6215(95)00401-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Division of Immunochemistry, Research Center Borstel, Borstel, Germany
  Methods: methylation, NMR, mild acid hydrolysis, de-O-acetylation, partial methanolysis
  
   
  
  Pseudomonas fluorescens ATCC 49271
  CSDB ID 2808 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192

• Article ID: 851
  Knirel YA, Helbig JH, Zähringer U "Structure of a decasaccharide isolated by mild acid degradation and dephosphorylation of the lipopolysaccharide of Pseudomonas fluorescens strain ATCC49271" - Carbohydrate Research 283 (1996) 129-139
  

  Mild acid degradation of the Pseudomonas fluorescens strain ATCC49271 lipopolysaccharide resulted in a core oligosaccharide containing D-glucose, 2-acetamido-2-deoxy-D-glucose, 2-(L- alanylamino)-2-deoxy-D-galactose, 2-acetamido-2,6-dideoxy-D-glucose (QuiNAc), 2-acetamido- 2,6-dideoxy-L-galactose (FucNAc), L-glycero-D-manno-heptose (Hep), 3-deoxy-D-manno-octulosonic acid (Kdo, present in multiple forms), and 5-acetamidino-7-acetamido-3,5,7,9- tetradeoxy- L-glycero-D-galacto-nonulosonic acid (a di-N-acyl derivative of legionaminic acid, Non) as well as O-acetyl, O-carbamoyl, and phosphate groups, including triphosphate groups. The dephosphorylated (HF) decasaccharide and products of its partial and full O-deacylation were studied by methylation analysis, GLC-MS, and 1H NMR spectroscopy, including 1D NOE and 2D shift-correlated spectroscopy (COSY). The core oligosaccharide of P. fluorescens strain ATCC49271 was found to be a decasaccharide (with partially degraded Kdo region) and one O-antigen repeating unit (di-N-acyllegionaminic acid, Non) attached. The following structure of the dephosphorylated core oligosaccharide was established: [sequence: see text]

  Lipopolysaccharide, structure, Pseudomonas, NMR spectroscopy, Pseudomonas fluorescens, core oligosacharide

  NCBI PubMed ID: 8901267
  Publication DOI: 10.1016/0008-6215(95)00401-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Division of Immunochemistry, Research Center Borstel, Borstel, Germany
  Methods: methylation, NMR, mild acid hydrolysis, de-O-acetylation, partial methanolysis
  
   
  
  Pseudomonas fluorescens ATCC 49271
  CSDB ID 2950 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192

• Article ID: 851
  Knirel YA, Helbig JH, Zähringer U "Structure of a decasaccharide isolated by mild acid degradation and dephosphorylation of the lipopolysaccharide of Pseudomonas fluorescens strain ATCC49271" - Carbohydrate Research 283 (1996) 129-139
  

  Mild acid degradation of the Pseudomonas fluorescens strain ATCC49271 lipopolysaccharide resulted in a core oligosaccharide containing D-glucose, 2-acetamido-2-deoxy-D-glucose, 2-(L- alanylamino)-2-deoxy-D-galactose, 2-acetamido-2,6-dideoxy-D-glucose (QuiNAc), 2-acetamido- 2,6-dideoxy-L-galactose (FucNAc), L-glycero-D-manno-heptose (Hep), 3-deoxy-D-manno-octulosonic acid (Kdo, present in multiple forms), and 5-acetamidino-7-acetamido-3,5,7,9- tetradeoxy- L-glycero-D-galacto-nonulosonic acid (a di-N-acyl derivative of legionaminic acid, Non) as well as O-acetyl, O-carbamoyl, and phosphate groups, including triphosphate groups. The dephosphorylated (HF) decasaccharide and products of its partial and full O-deacylation were studied by methylation analysis, GLC-MS, and 1H NMR spectroscopy, including 1D NOE and 2D shift-correlated spectroscopy (COSY). The core oligosaccharide of P. fluorescens strain ATCC49271 was found to be a decasaccharide (with partially degraded Kdo region) and one O-antigen repeating unit (di-N-acyllegionaminic acid, Non) attached. The following structure of the dephosphorylated core oligosaccharide was established: [sequence: see text]

  Lipopolysaccharide, structure, Pseudomonas, NMR spectroscopy, Pseudomonas fluorescens, core oligosacharide

  NCBI PubMed ID: 8901267
  Publication DOI: 10.1016/0008-6215(95)00401-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Division of Immunochemistry, Research Center Borstel, Borstel, Germany
  Methods: methylation, NMR, mild acid hydrolysis, de-O-acetylation, partial methanolysis
  
   
  
  Pseudomonas fluorescens ATCC 49271
  CSDB ID 2951 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192

• Article ID: 851
  Knirel YA, Helbig JH, Zähringer U "Structure of a decasaccharide isolated by mild acid degradation and dephosphorylation of the lipopolysaccharide of Pseudomonas fluorescens strain ATCC49271" - Carbohydrate Research 283 (1996) 129-139
  

  Mild acid degradation of the Pseudomonas fluorescens strain ATCC49271 lipopolysaccharide resulted in a core oligosaccharide containing D-glucose, 2-acetamido-2-deoxy-D-glucose, 2-(L- alanylamino)-2-deoxy-D-galactose, 2-acetamido-2,6-dideoxy-D-glucose (QuiNAc), 2-acetamido- 2,6-dideoxy-L-galactose (FucNAc), L-glycero-D-manno-heptose (Hep), 3-deoxy-D-manno-octulosonic acid (Kdo, present in multiple forms), and 5-acetamidino-7-acetamido-3,5,7,9- tetradeoxy- L-glycero-D-galacto-nonulosonic acid (a di-N-acyl derivative of legionaminic acid, Non) as well as O-acetyl, O-carbamoyl, and phosphate groups, including triphosphate groups. The dephosphorylated (HF) decasaccharide and products of its partial and full O-deacylation were studied by methylation analysis, GLC-MS, and 1H NMR spectroscopy, including 1D NOE and 2D shift-correlated spectroscopy (COSY). The core oligosaccharide of P. fluorescens strain ATCC49271 was found to be a decasaccharide (with partially degraded Kdo region) and one O-antigen repeating unit (di-N-acyllegionaminic acid, Non) attached. The following structure of the dephosphorylated core oligosaccharide was established: [sequence: see text]

  Lipopolysaccharide, structure, Pseudomonas, NMR spectroscopy, Pseudomonas fluorescens, core oligosacharide

  NCBI PubMed ID: 8901267
  Publication DOI: 10.1016/0008-6215(95)00401-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: uzaehr@fz-borstel.de
  Institutions: Division of Immunochemistry, Research Center Borstel, Borstel, Germany
  Methods: methylation, NMR, mild acid hydrolysis, de-O-acetylation, partial methanolysis
  
   
  
  Pseudomonas fluorescens ATCC 49271
  CSDB ID 2952 (all data & tools)