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1. Compound ID: 139
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a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ P-2)-+ a-Kdop-(2-4)-+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: glycoform 1 core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 29
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Lindner B, Zähringer U, Pier GB "Structural studies on the core and the O-polysaccharide repeating unit of Pseudomonas aeruginosa immunotype 1 lipopolysaccharide" -
European Journal of Biochemistry 269(8) (2002) 2194-2203
The structure of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 1 was studied after mild acid and strong alkaline degradations by MS and NMR spectroscopy. Three types of LPS molecules were found, including those with an unsubstituted glycoform 1 core (A) or an isomeric glycoform 2 core substituted with one O-polysaccharide repeating unit (B) or with a long-chain O-polysaccharide. Therefore, of two core glycoforms, only glycoform 2 accepts the O-polysaccharide. In the structures A and B, Kdo, Hep, Hep7Cm, GalNAcAN3Ac, GalNFoAN, QuiNAc, GalNAla represent 3-deoxy-d-manno-octulosonic acid, l-glycero-d-manno-heptose, 7-O-carbamoyl-l-glycero-d-manno-heptose, 2-acetamido-3-O-acetyl-2-deoxygalacturonamide, 2-formamido-2-deoxygalacturonamide, 2-acetamido-2,6-dideoxyglucose and 2-(l-alanylamino)-2-deoxygalactose, respectively; all sugars are in the pyranose form and have the d configuration unless otherwise stated. One or more phosphorylation sites may be occupied by diphosphate groups. In a minority of the LPS molecules, an O-acetyl group is present in the outer core region at unknown position. The site and the configuration of the linkage between the O-polysaccharide and the core and the structure of the O-polysaccharide repeating unit were defined in P. aeruginosa immunotype 1. The QuiNAc residue linked to the Rha residue of the core was found to have the beta configuration, whereas in the interior repeating units of the O-polysaccharide this residue is in the α-configuration. The data obtained are in accordance with the initiation of biosynthesis of the O-polysaccharide of P. aeruginosa O6, which is closely related to immunotype 1, by transfer of d-QuiNAc-1-P to undecaprenyl phosphate followed by synthesis of the repeating O-antigen tetrasaccharide
Lipopolysaccharide, structure, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, O-polysaccharide
NCBI PubMed ID: 11985598Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
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, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation
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2. Compound ID: 141
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a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ P-2)-+ a-Kdop-(2-4)-+ P-4)-+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(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-(1-P
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P-4)-+ |
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Structure type: oligomer
Trivial name: glycoform 1, glycoform 1 core, glycoform 1a, uncapped core oligosaccharide
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 29
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Lindner B, Zähringer U, Pier GB "Structural studies on the core and the O-polysaccharide repeating unit of Pseudomonas aeruginosa immunotype 1 lipopolysaccharide" -
European Journal of Biochemistry 269(8) (2002) 2194-2203
The structure of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 1 was studied after mild acid and strong alkaline degradations by MS and NMR spectroscopy. Three types of LPS molecules were found, including those with an unsubstituted glycoform 1 core (A) or an isomeric glycoform 2 core substituted with one O-polysaccharide repeating unit (B) or with a long-chain O-polysaccharide. Therefore, of two core glycoforms, only glycoform 2 accepts the O-polysaccharide. In the structures A and B, Kdo, Hep, Hep7Cm, GalNAcAN3Ac, GalNFoAN, QuiNAc, GalNAla represent 3-deoxy-d-manno-octulosonic acid, l-glycero-d-manno-heptose, 7-O-carbamoyl-l-glycero-d-manno-heptose, 2-acetamido-3-O-acetyl-2-deoxygalacturonamide, 2-formamido-2-deoxygalacturonamide, 2-acetamido-2,6-dideoxyglucose and 2-(l-alanylamino)-2-deoxygalactose, respectively; all sugars are in the pyranose form and have the d configuration unless otherwise stated. One or more phosphorylation sites may be occupied by diphosphate groups. In a minority of the LPS molecules, an O-acetyl group is present in the outer core region at unknown position. The site and the configuration of the linkage between the O-polysaccharide and the core and the structure of the O-polysaccharide repeating unit were defined in P. aeruginosa immunotype 1. The QuiNAc residue linked to the Rha residue of the core was found to have the beta configuration, whereas in the interior repeating units of the O-polysaccharide this residue is in the α-configuration. The data obtained are in accordance with the initiation of biosynthesis of the O-polysaccharide of P. aeruginosa O6, which is closely related to immunotype 1, by transfer of d-QuiNAc-1-P to undecaprenyl phosphate followed by synthesis of the repeating O-antigen tetrasaccharide
Lipopolysaccharide, structure, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, O-polysaccharide
NCBI PubMed ID: 11985598Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
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, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation
- Article ID: 31
Bystrova OV, Lindner B, Moll H, Kocharova NA, Knirel YA, Zähringer U, Pier GB "Structure of the biological repeating unit of the O-antigen of Pseudomonas aeruginosa immunotype 4 containing both 2-acetamido-2,6-dideoxy-D-glucose and 2-acetamido-2,6-dideoxy-D-galactose" -
Carbohydrate Research 338(17) (2003) 1801-1806
A phosphorylated core-lipid A backbone oligosaccharide that carries a disaccharide remainder of the first O-antigen repeating unit was derived by strong alkaline degradation following mild hydrazinolysis of the lipopolysaccharide of Pseudomonas aeruginosa immunotype 4 (serogroup O-1). The structure of the oligosaccharide was determined using ESI MS and NMR spectroscopy and it was demonstrated that 2-acetamido-2,6-dideoxy-D-glucose is the first monosaccharide of the O-polysaccharide that is linked to the LPS core. These data define the structure of the biological repeating unit of the O-antigen
Lipopolysaccharide, structure, O-antigen, repeating unit, Pseudomonas aeruginosa, O-polysaccharide, 2-acetamido-2, 6-dideoxy-D-galactose
NCBI PubMed ID: 12892948Publication DOI: 10.1016/S0008-6215(03)00262-3Journal NLM ID: 0043535Publisher: 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, 31P NMR, ESI-MS, GLC, alkaline degradation
- Article ID: 32
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: 12932374Publication DOI: 10.1016/S0008-6215(03)00290-8Journal NLM ID: 0043535Publisher: 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, GLC, mild acid hydrolysis, alkaline degradation, HPAEC, ESI-FT-MS
- Article ID: 3207
Bystrova OV, Knirel YA, Lindner B, Kocharova NA, Kondakova AN, Zähringer U, Pier GB "Structures of the core oligosaccharide and O-units in the R- and SR-type lipopolysaccharides of reference strains of Pseudomonas aeruginosa O-serogroups" -
FEMS Immunology and Medical Microbiology 46(1) (2006) 85-99
Highly phosphorylated core oligosaccharides and those substituted with one O-antigen repeating unit were obtained by mild acid degradation or strong alkaline hydrolysis of lipopolysaccharide samples from 23 reference strains representing all Pseudomonas aeruginosa O-serogroups. Studies by high-resolution electrospray ionization mass spectrometry and two-dimensional NMR spectroscopy revealed both conserved and variable structural features of the lipopolysaccharides of various O-serogroups. The upstream terminal saccharide of the O-antigen, which contributes most to the immunospecificity of the bacteria, was defined in 11 from a total of 13 O-serogroups. The data obtained link together the known biosynthesis pathways, genetics and serology of the P. aeruginosa lipopolysaccharide.
lipopolysaccharides, oligosaccharide, structure, core, strain, O-antigen, Pseudomonas, Pseudomonas aeruginosa, core oligosaccharide, reference, lipopolysaccharide structure, preparation, PDF, O-unit
NCBI PubMed ID: 16420601Publication DOI: 10.1111/j.1574-695X.2005.00004.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: olgabv@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, Channing Laboratory, Department of Medicine, Brigham and Women’s Hospital, Harvard Medical School, Boston,MA, USA
Methods: NMR-2D, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
- Article ID: 4051
Kocincova D, Hao Y, Vinogradov E, Lam JS "Evidence that WapB is an 1,2 glucosyltransferase of Pseudomonas aeruginosa involved in LPS outer core biosynthesis" -
Journal of Bacteriology 193(11) (2011) 2708-2716
Pseudomonas aeruginosa is an important opportunistic pathogen infecting debilitated individuals. One of the major virulence factors elaborated by P. aeruginosa is lipopolysaccharide (LPS), which is composed of lipid A, core oligosaccharide (OS) and O-antigen polysaccharide. The core OS is divided into inner and outer regions. Although the structure of the outer core OS has been elucidated, the functions and mechanisms of the glycosyltransferases involved in core OS biogenesis is currently unknown. Here, we show that a previously uncharacterised gene pa1014 is involved in outer core biosynthesis and we propose to rename this gene as wapB. We constructed a chromosomal mutant wapB::Gm in strain PAO1 (O5 serotype) background. Characterization of the LPS from the mutant by Western immunoblotting showed a lack of reactivity to PAO1 outer core-specific monoclonal antibody (MAb) 5c-101. The chemical structure of the core OS of the wapB mutant was elucidated using nuclear magnetic resonance spectroscopy and mass spectrometry techniques and revealed that the core OS of the wapB mutant lacked the terminal β-1,2-linked-D-glucose residue. Complementation of the mutant with wapB in trans restored the core structure to one that is identical to the wildtype. Eleven of the twenty P. aeruginosa IATS serotypes produce LPS that lack the terminal D-glucose residue (Glc(IV)). Interestingly, expression of wapB in each of these eleven serotypes lacking Glc(IV) has modified each of their outer core OS structures, which became reactive to MAb 5c101 in Western immunoblotting suggesting the presence of a terminal D-glucose in these core OS structures. Our results strongly suggested that wapB encodes an 1,2-glucosyltransferase.
Lipopolysaccharide, biosynthesis, O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, glycosyltransferase, immunoblotting
NCBI PubMed ID: 21441506Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: jlam@uoguelph.ca
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0A6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, DNA techniques, alkaline degradation, Western blotting, de-O-acylation with hydrazine, genetic methods, CE-MS
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
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3. Compound ID: 144
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-+ P-6)-+ P-2)-+ a-Kdop-(2-4)-+ P-4)-+
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b-D-Glcp-(1-2)-a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-a-D-GalpN-(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-(1-P
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P-4)-+ |
Show graphically |
Structure type: oligomer
Trivial name: glycoform 1, glycoform 1b, uncapped core oligosaccharide
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 30
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Zähringer U, Pier GB "Elucidation of the structure of the lipopolysaccharide core and the linkage between the core and the O-antigen in Pseudomonas aeruginosa immunotype 5 using strong alkaline degradation of the lipopolysaccharide" -
Biochemistry (Moscow) 68(8) (2003) 918-925
The products of the strong alkaline degradation of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 5 were separated by anion-exchange HPLC and studied by electrospray ionization mass spectrometry and NMR spectroscopy. It was found that two major products have the same inner core region and lipid A carbohydrate backbone but different outer core regions. The difference is in the position of a rhamnose residue, which is substituted with either an additional glucose residue or a disaccharide remainder of the degraded O-polysaccharide. The site and the configuration of the linkage between the O-polysaccharide and the core were determined and, together with published data, the structure of the so-called biological repeating unit of the O-antigen was defined. The glycosidic linkage of the 2-acetamido-2,6-dideoxy-D-glucose (N-acetyl-D-quinovosamine) residue is ? when it links the O-polysaccharide to the core and ? when it connects the interior repeating units of the O-polysaccharide to each other
Lipopolysaccharide, O-antigen, repeating unit, Pseudomonas aeruginosa, core oligosaccharide
NCBI PubMed ID: 12948393Publication DOI: 10.1023/a:1025759217501Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
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, 31P NMR, ESI-MS, GLC, alkaline degradation
- Article ID: 500
Bystrova OV, Lindner B, Moll H, Kocharova NA, Shashkov AS, Knirel YA, Zähringer U, Pier GB "Full structure of the lipopolysaccharide of Pseudomonas aeruginosa immunotype 5" -
Biochemistry (Moscow) 69(2) (2004) 170-175
The lipopolysaccharide (LPS) of the opportunistic human pathogen Pseudomonas aeruginosa immunotype 5 was delipidated by mild acid hydrolysis, and the products were separated by high-performance anion-exchange chromatography and analyzed by ESI MS and NMR spectroscopy. LPS species of three types were found, including those with an unsubstituted core and the core substituted with one O-polysaccharide repeating unit or with an O-polysaccharide of a variable number of repeating units. The core region is highly phosphorylated, the major species containing two monophosphate groups and one ethanolamine diphosphate group. Based on these and published data on the O-polysaccharide structure, the full structure of the LPS of P. aeruginosa immunotype 5 was established.
Lipopolysaccharide, O-antigen, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, ethanolamine diphosphate
NCBI PubMed ID: 15000683Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, USA
Methods: NMR-2D, NMR, ESI-MS, HPAEC
- Article ID: 3207
Bystrova OV, Knirel YA, Lindner B, Kocharova NA, Kondakova AN, Zähringer U, Pier GB "Structures of the core oligosaccharide and O-units in the R- and SR-type lipopolysaccharides of reference strains of Pseudomonas aeruginosa O-serogroups" -
FEMS Immunology and Medical Microbiology 46(1) (2006) 85-99
Highly phosphorylated core oligosaccharides and those substituted with one O-antigen repeating unit were obtained by mild acid degradation or strong alkaline hydrolysis of lipopolysaccharide samples from 23 reference strains representing all Pseudomonas aeruginosa O-serogroups. Studies by high-resolution electrospray ionization mass spectrometry and two-dimensional NMR spectroscopy revealed both conserved and variable structural features of the lipopolysaccharides of various O-serogroups. The upstream terminal saccharide of the O-antigen, which contributes most to the immunospecificity of the bacteria, was defined in 11 from a total of 13 O-serogroups. The data obtained link together the known biosynthesis pathways, genetics and serology of the P. aeruginosa lipopolysaccharide.
lipopolysaccharides, oligosaccharide, structure, core, strain, O-antigen, Pseudomonas, Pseudomonas aeruginosa, core oligosaccharide, reference, lipopolysaccharide structure, preparation, PDF, O-unit
NCBI PubMed ID: 16420601Publication DOI: 10.1111/j.1574-695X.2005.00004.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: olgabv@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, Channing Laboratory, Department of Medicine, Brigham and Women’s Hospital, Harvard Medical School, Boston,MA, USA
Methods: NMR-2D, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
- Article ID: 4051
Kocincova D, Hao Y, Vinogradov E, Lam JS "Evidence that WapB is an 1,2 glucosyltransferase of Pseudomonas aeruginosa involved in LPS outer core biosynthesis" -
Journal of Bacteriology 193(11) (2011) 2708-2716
Pseudomonas aeruginosa is an important opportunistic pathogen infecting debilitated individuals. One of the major virulence factors elaborated by P. aeruginosa is lipopolysaccharide (LPS), which is composed of lipid A, core oligosaccharide (OS) and O-antigen polysaccharide. The core OS is divided into inner and outer regions. Although the structure of the outer core OS has been elucidated, the functions and mechanisms of the glycosyltransferases involved in core OS biogenesis is currently unknown. Here, we show that a previously uncharacterised gene pa1014 is involved in outer core biosynthesis and we propose to rename this gene as wapB. We constructed a chromosomal mutant wapB::Gm in strain PAO1 (O5 serotype) background. Characterization of the LPS from the mutant by Western immunoblotting showed a lack of reactivity to PAO1 outer core-specific monoclonal antibody (MAb) 5c-101. The chemical structure of the core OS of the wapB mutant was elucidated using nuclear magnetic resonance spectroscopy and mass spectrometry techniques and revealed that the core OS of the wapB mutant lacked the terminal β-1,2-linked-D-glucose residue. Complementation of the mutant with wapB in trans restored the core structure to one that is identical to the wildtype. Eleven of the twenty P. aeruginosa IATS serotypes produce LPS that lack the terminal D-glucose residue (Glc(IV)). Interestingly, expression of wapB in each of these eleven serotypes lacking Glc(IV) has modified each of their outer core OS structures, which became reactive to MAb 5c101 in Western immunoblotting suggesting the presence of a terminal D-glucose in these core OS structures. Our results strongly suggested that wapB encodes an 1,2-glucosyltransferase.
Lipopolysaccharide, biosynthesis, O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, glycosyltransferase, immunoblotting
NCBI PubMed ID: 21441506Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: jlam@uoguelph.ca
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0A6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, DNA techniques, alkaline degradation, Western blotting, de-O-acylation with hydrazine, genetic methods, CE-MS
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4. Compound ID: 153
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a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ EtN-(1--P--2)--+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
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L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Trivial name: glycoform 1 core
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 32
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: 12932374Publication DOI: 10.1016/S0008-6215(03)00290-8Journal NLM ID: 0043535Publisher: 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, GLC, mild acid hydrolysis, alkaline degradation, HPAEC, ESI-FT-MS
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5. Compound ID: 1408
|
a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ P-2)-+ a-Kdop-(2-4)-+ P-4)-+
| | | | |
b-D-GlcpN-(1-2)-b-D-Glcp-(1-3)-a-D-GalpN-(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-(1-P
|
P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 439
Zdorovenko EL, Vinogradov EV, Zdorovenko GM, Lindner B, Bystrova OV, Shashkov AS, Rudolph K, Zähringer U, Knirel YA "Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolicola" -
European Journal of Biochemistry 271(23-24) (2004) 4968-4977
The core structure of the lipopolysaccharide (LPS) isolated from a rough strain of the phytopathogenic bacterium Pseudomonas syringae pv. phaseolicola, GSPB 711, was investigated by sugar and methylation analyses, Fourier transform ion-cyclotron resonance ESI MS, and one- and two-dimensional (1)H-, (13)C- and (31)P-NMR spectroscopy. Strong alkaline deacylation of the LPS resulted in two core-lipid A backbone undecasaccharide pentakisphosphates in the ratio approximately 2.5 : 1, which corresponded to outer core glycoforms 1 and 2 terminated with either l-rhamnose or 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), respectively. Mild acid degradation of the LPS gave the major glycoform 1 core octasaccharide and a minor truncated glycoform 2 core heptasaccharide, which resulted from the cleavage of the terminal Kdo residues. The inner core of P. syringae is distinguished by a high degree of phosphorylation of l-glycero-d-manno-heptose residues with phosphate, diphosphate and ethanolamine diphosphate groups. The glycoform 1 core is structurally similar but not identical to one of the core glycoforms of the human pathogenic bacterium Pseudomonas aeruginosa. The outer core composition and structure may be useful as a chemotaxonomic marker for the P. syringae group of bacteria, whereas a more conserved inner core structure appears to be representative for the whole genus Pseudomonas
structure, core oligosaccharide, Pseudomonas syringae, glycoform, ipopolysaccharide, phytopathogen
NCBI PubMed ID: 15606785Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Moscow, Russia, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine, Institute for Plant Pathology and Plant Defence, Georg August University, Gottingen, Germany
Methods: NMR-2D, methylation, NMR, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
- Article ID: 6095
Kutschera A, Schombel U, Schwudke D, Ranf S, Gisch N "Analysis of the Structure and Biosynthesis of the Lipopolysaccharide Core Oligosaccharide of Pseudomonas syringae pv. tomato DC3000" -
International Journal of Molecular Sciences 22(6) (2021) 3250
Lipopolysaccharide (LPS), the major component of the outer membrane of Gram-negative bacteria, is important for bacterial viability in general and host-pathogen interactions in particular. Negative charges at its core oligosaccharide (core-OS) contribute to membrane integrity through bridging interactions with divalent cations. The molecular structure and synthesis of the core-OS have been resolved in various bacteria including the mammalian pathogen Pseudomonas aeruginosa. A few core-OS structures of plant-associated Pseudomonas strains have been solved to date, but the genetic components of the underlying biosynthesis remained unclear. We conducted a comparative genome analysis of the core-OS gene cluster in Pseudomonas syringae pv. tomato (Pst) DC3000, a widely used model pathogen in plant-microbe interactions, within the P. syringae species complex and to other plant-associated Pseudomonas strains. Our results suggest a genetic and structural conservation of the inner core-OS but variation in outer core-OS composition within the P. syringae species complex. Structural analysis of the core-OS of Pst DC3000 shows an uncommonly high phosphorylation and presence of an O-acetylated sugar. Finally, we combined the results of our genomic survey with available structure information to estimate the core-OS composition of other Pseudomonas species.
Lipopolysaccharide, core oligosaccharide, NMR spectroscopy, mass spectrometry, Pseudomonas syringae, Structural characterization
NCBI PubMed ID: 33806795Publication DOI: 10.3390/ijms22063250Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: Stefanie Ranf
; Nicolas Gisch
Institutions: Chair of Phytopathology, TUM School of Life Sciences Weihenstephan, Technical University of Munich, 85354 Freising-Weihenstephan, Germany, Division of Bioanalytical Chemistry, Priority Area Infections, Research Center Borstel, Leibniz Lung Center, Parkallee 1-40, 23845 Borstel, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, sugar analysis, 31P NMR, mild acid hydrolysis, HPAEC, MS, de-O-acylation with hydrazine, GPC, alkaline hydrolysis, de-N-acylation, bioinformatic analysis
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6. Compound ID: 1510
|
a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ P-2)-+
| | |
b-D-GlcpNAc-(1-2)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
| |
L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 439
Zdorovenko EL, Vinogradov EV, Zdorovenko GM, Lindner B, Bystrova OV, Shashkov AS, Rudolph K, Zähringer U, Knirel YA "Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolicola" -
European Journal of Biochemistry 271(23-24) (2004) 4968-4977
The core structure of the lipopolysaccharide (LPS) isolated from a rough strain of the phytopathogenic bacterium Pseudomonas syringae pv. phaseolicola, GSPB 711, was investigated by sugar and methylation analyses, Fourier transform ion-cyclotron resonance ESI MS, and one- and two-dimensional (1)H-, (13)C- and (31)P-NMR spectroscopy. Strong alkaline deacylation of the LPS resulted in two core-lipid A backbone undecasaccharide pentakisphosphates in the ratio approximately 2.5 : 1, which corresponded to outer core glycoforms 1 and 2 terminated with either l-rhamnose or 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), respectively. Mild acid degradation of the LPS gave the major glycoform 1 core octasaccharide and a minor truncated glycoform 2 core heptasaccharide, which resulted from the cleavage of the terminal Kdo residues. The inner core of P. syringae is distinguished by a high degree of phosphorylation of l-glycero-d-manno-heptose residues with phosphate, diphosphate and ethanolamine diphosphate groups. The glycoform 1 core is structurally similar but not identical to one of the core glycoforms of the human pathogenic bacterium Pseudomonas aeruginosa. The outer core composition and structure may be useful as a chemotaxonomic marker for the P. syringae group of bacteria, whereas a more conserved inner core structure appears to be representative for the whole genus Pseudomonas
structure, core oligosaccharide, Pseudomonas syringae, glycoform, ipopolysaccharide, phytopathogen
NCBI PubMed ID: 15606785Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Moscow, Russia, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine, Institute for Plant Pathology and Plant Defence, Georg August University, Gottingen, Germany
Methods: NMR-2D, methylation, NMR, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
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7. Compound ID: 1511
|
a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-6)-+ EtN-(1--P--2)--+
| | |
b-D-GlcpNAc-(1-2)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
| |
L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 439
Zdorovenko EL, Vinogradov EV, Zdorovenko GM, Lindner B, Bystrova OV, Shashkov AS, Rudolph K, Zähringer U, Knirel YA "Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolicola" -
European Journal of Biochemistry 271(23-24) (2004) 4968-4977
The core structure of the lipopolysaccharide (LPS) isolated from a rough strain of the phytopathogenic bacterium Pseudomonas syringae pv. phaseolicola, GSPB 711, was investigated by sugar and methylation analyses, Fourier transform ion-cyclotron resonance ESI MS, and one- and two-dimensional (1)H-, (13)C- and (31)P-NMR spectroscopy. Strong alkaline deacylation of the LPS resulted in two core-lipid A backbone undecasaccharide pentakisphosphates in the ratio approximately 2.5 : 1, which corresponded to outer core glycoforms 1 and 2 terminated with either l-rhamnose or 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), respectively. Mild acid degradation of the LPS gave the major glycoform 1 core octasaccharide and a minor truncated glycoform 2 core heptasaccharide, which resulted from the cleavage of the terminal Kdo residues. The inner core of P. syringae is distinguished by a high degree of phosphorylation of l-glycero-d-manno-heptose residues with phosphate, diphosphate and ethanolamine diphosphate groups. The glycoform 1 core is structurally similar but not identical to one of the core glycoforms of the human pathogenic bacterium Pseudomonas aeruginosa. The outer core composition and structure may be useful as a chemotaxonomic marker for the P. syringae group of bacteria, whereas a more conserved inner core structure appears to be representative for the whole genus Pseudomonas
structure, core oligosaccharide, Pseudomonas syringae, glycoform, ipopolysaccharide, phytopathogen
NCBI PubMed ID: 15606785Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Moscow, Russia, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine, Institute for Plant Pathology and Plant Defence, Georg August University, Gottingen, Germany
Methods: NMR-2D, methylation, NMR, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
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8. Compound ID: 1514
|
a-L-Rhap-(1-6)-b-D-Glcp-(1-4)-+ P-6)-+ EtN-(1-0)-?%P---P--2)-+ a-Kdop-(2-4)-+
| | | |
b-D-GlcpNAc-(1-2)-a-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/
| |
L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide glycoform I
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 439
Zdorovenko EL, Vinogradov EV, Zdorovenko GM, Lindner B, Bystrova OV, Shashkov AS, Rudolph K, Zähringer U, Knirel YA "Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolicola" -
European Journal of Biochemistry 271(23-24) (2004) 4968-4977
The core structure of the lipopolysaccharide (LPS) isolated from a rough strain of the phytopathogenic bacterium Pseudomonas syringae pv. phaseolicola, GSPB 711, was investigated by sugar and methylation analyses, Fourier transform ion-cyclotron resonance ESI MS, and one- and two-dimensional (1)H-, (13)C- and (31)P-NMR spectroscopy. Strong alkaline deacylation of the LPS resulted in two core-lipid A backbone undecasaccharide pentakisphosphates in the ratio approximately 2.5 : 1, which corresponded to outer core glycoforms 1 and 2 terminated with either l-rhamnose or 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), respectively. Mild acid degradation of the LPS gave the major glycoform 1 core octasaccharide and a minor truncated glycoform 2 core heptasaccharide, which resulted from the cleavage of the terminal Kdo residues. The inner core of P. syringae is distinguished by a high degree of phosphorylation of l-glycero-d-manno-heptose residues with phosphate, diphosphate and ethanolamine diphosphate groups. The glycoform 1 core is structurally similar but not identical to one of the core glycoforms of the human pathogenic bacterium Pseudomonas aeruginosa. The outer core composition and structure may be useful as a chemotaxonomic marker for the P. syringae group of bacteria, whereas a more conserved inner core structure appears to be representative for the whole genus Pseudomonas
structure, core oligosaccharide, Pseudomonas syringae, glycoform, ipopolysaccharide, phytopathogen
NCBI PubMed ID: 15606785Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Moscow, Russia, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine, Institute for Plant Pathology and Plant Defence, Georg August University, Gottingen, Germany
Methods: NMR-2D, methylation, NMR, mild acid hydrolysis, alkaline degradation, ESI-FTICR-MS
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9. Compound ID: 1619
|
a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-+ P-6)-+ EtN-(1---P---P---2)-+
| | |
b-D-Glcp-(1-2)-a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
| |
L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 500
Bystrova OV, Lindner B, Moll H, Kocharova NA, Shashkov AS, Knirel YA, Zähringer U, Pier GB "Full structure of the lipopolysaccharide of Pseudomonas aeruginosa immunotype 5" -
Biochemistry (Moscow) 69(2) (2004) 170-175
The lipopolysaccharide (LPS) of the opportunistic human pathogen Pseudomonas aeruginosa immunotype 5 was delipidated by mild acid hydrolysis, and the products were separated by high-performance anion-exchange chromatography and analyzed by ESI MS and NMR spectroscopy. LPS species of three types were found, including those with an unsubstituted core and the core substituted with one O-polysaccharide repeating unit or with an O-polysaccharide of a variable number of repeating units. The core region is highly phosphorylated, the major species containing two monophosphate groups and one ethanolamine diphosphate group. Based on these and published data on the O-polysaccharide structure, the full structure of the LPS of P. aeruginosa immunotype 5 was established.
Lipopolysaccharide, O-antigen, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, ethanolamine diphosphate
NCBI PubMed ID: 15000683Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, USA
Methods: NMR-2D, NMR, ESI-MS, HPAEC
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10. Compound ID: 1620
|
a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-+ P-6)-+ EtN-(1---P---P---2)-+ a-Kdop-(2-4)-+
| | | |
b-D-Glcp-(1-2)-a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdo-(2--/lipid A/
| |
L-Ala-(1-2)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 500
Bystrova OV, Lindner B, Moll H, Kocharova NA, Shashkov AS, Knirel YA, Zähringer U, Pier GB "Full structure of the lipopolysaccharide of Pseudomonas aeruginosa immunotype 5" -
Biochemistry (Moscow) 69(2) (2004) 170-175
The lipopolysaccharide (LPS) of the opportunistic human pathogen Pseudomonas aeruginosa immunotype 5 was delipidated by mild acid hydrolysis, and the products were separated by high-performance anion-exchange chromatography and analyzed by ESI MS and NMR spectroscopy. LPS species of three types were found, including those with an unsubstituted core and the core substituted with one O-polysaccharide repeating unit or with an O-polysaccharide of a variable number of repeating units. The core region is highly phosphorylated, the major species containing two monophosphate groups and one ethanolamine diphosphate group. Based on these and published data on the O-polysaccharide structure, the full structure of the LPS of P. aeruginosa immunotype 5 was established.
Lipopolysaccharide, O-antigen, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, ethanolamine diphosphate
NCBI PubMed ID: 15000683Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, USA
Methods: NMR-2D, NMR, ESI-MS, HPAEC
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11. Compound ID: 1718
|
a-L-Rhap-(1-6)-b-D-Glcp-(1-6)-a-D-Glcp-(1-4)-b-D-GlcpA-(1-2)-a-D-Manp6Ac-(1-3)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Glcp6Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: acetan
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_136105,IEDB_140630,IEDB_141806,IEDB_142488,IEDB_144144,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 529
Ridout M, Cairns P, Brownsey G, Morris V "Synergistic interactions between the genetically modified bacterial polysaccharide P2 and carob or konjac mannan" -
Carbohydrate Research 339(13) (2004) 2233-2239
Rheological studies have confirmed that the bacterial polysaccharide P2, a genetically modified variant of the Acetobacter xylinum polysaccharide acetan, undergoes synergistic gelation with either of the plant polysaccharides carob or konjac mannan. X-ray fibre diffraction data shows that P2 can form a 5-fold helical structure of pitch 4.7nm and an axial rise per disaccharide repeat of 0.92nm. Optical rotation data demonstrate that P2 undergoes a coil-helix transition in solution and that deacylation enhances the stability of the helical structure in solution. Studies made on mixtures prepared at different temperatures and ionic strengths suggest that denaturation of the P2 helix favours interaction and gelation. Deacetylation of P2 enhances gelation. X-ray diffraction data for oriented fibres prepared from deacetylated P2-konjac mannan mixed films reveal a 6-fold helical structure of pitch 5.54nm with an axial rise per disaccharide repeat also of 0.92nm. This mixed helix provides direct evidence for binding between the two polysaccharides. P2 contains two sites of acetylation: one on the backbone and one on the sidechain. The former site of acetylation inhibits helix formation for P2. It is suggested that this site of acetylation also inhibits formation of the mixed helix, explaining the enhanced gelation of mixtures on deacetylation.
Bacterial polysaccharide, Rheology, Konjac mannan, Mixtures, Carob
NCBI PubMed ID: 15337451Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: geoff.brownsey@bbsrc.ac.uk
Institutions: Institute of Food Research, Food Material Science, Norwich Research Park, Colney, Norwich, UK
Methods: X-ray, optical rotation measurement
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 6151
Trček J, Dodsa I, Accetto T, Stopar D "Acetan and Acetan-Like Polysaccharides: Genetics, Biosynthesis, Structure, and Viscoelasticity" -
Polymers 13(5) (2021) 815
Bacteria produce a variety of multifunctional polysaccharides, including structural, intracellular, and extracellular polysaccharides. They are attractive for the industrial sector due to their natural origin, sustainability, biodegradability, low toxicity, stability, unique viscoelastic properties, stable cost, and supply. When incorporated into different matrices, they may control emulsification, stabilization, crystallization, water release, and encapsulation. Acetan is an important extracellular water-soluble polysaccharide produced mainly by bacterial species of the genera Komagataeibacter and Acetobacter. Since its original description in Komagataeibacter xylinus, acetan-like polysaccharides have also been described in other species of acetic acid bacteria. Our knowledge on chemical composition of different acetan-like polysaccharides, their viscoelasticity, and the genetic basis for their production has expanded during the last years. Here, we review data on acetan biosynthesis, its molecular structure, genetic organization, and mechanical properties. In addition, we have performed an extended bioinformatic analysis on acetan-like polysaccharide genetic clusters in the genomes of Komagataeibacter and Acetobacter species. The analysis revealed for the first time a second acetan-like polysaccharide genetic cluster, that is widespread in both genera. All species of the Komagataeibacter possess at least one acetan genetic cluster, while it is present in only one third of the Acetobacter species surveyed.
extracellular polysaccharide, Acetobacter, acetan, acetan-like polysaccharide, acetan-like polysaccharide genetic cluster, acetan genetic cluster, acetan structure, acetan synthesis, acetan viscoelasticity, applications of acetan, Komagataeibacter
NCBI PubMed ID: 33799945Publication DOI: 10.3390/polym13050815Journal NLM ID: 101545357Publisher: Basel: MDPI
Correspondence: janja.trcek@um.si
Institutions: Department of Biology, Faculty of Natural Sciences and Mathematics, University of Maribor, SI-2000 Maribor, Slovenia, Faculty of Chemistry and Chemical Engineering, University of Maribor, SI-2000 Maribor, Slovenia, Department of Food Science and Technology, Biotechnical Faculty, University of Ljubljana, SI-1000 Ljubljana, Slovenia, Animal Science Department, Biotechnical Faculty, University of Ljubljana, Domžale, Slovenia
- Article ID: 6303
Rath T, Ruhmann B, Sieber V "Systematic optimization of exopolysaccharide production by Gluconacetobacter sp. and use of (crude) glycerol as carbon source" -
Carbohydrate Polymers 276 (2022) 118769
The usage of polysaccharides as biodegradable polymers is of growing interest in the context of a sustainable and ecofriendly economy. For this, the production of exopolysaccharides (EPS) by Gluconacetobacter sp. was investigated. Glycerol as carbon source revealed to be beneficial compared to glucose. In addition, pure glycerol could be substituted by a crude glycerol waste stream from biodiesel production. Systematic analysis of the peptone and phosphate concentrations in glycerol-based media indicated a strong effect of peptone. Optimized parameters resulted in a titer of 25.4 ± 2.4 g/L EPS with a productivity of 0.46 ± 0.04 g*(L*h)-1. With decreasing peptone, a variation in the monomer ratios was observed. An accompanying change in molecular size distribution indicated the production of two different polysaccharides. Intensified analysis revealed the main polysaccharide to be composed of glucose (Glc), galactose (Gal), mannose (Man) and glucuronic acid (GlcA), and the minor polysaccharide of Gal, Man, ribose (Rib).
exopolysaccharide, optimization
NCBI PubMed ID: 34823788Publication DOI: 10.1016/j.carbpol.2021.118769Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: V. Sieber
Institutions: Chair of Chemistry of Biogenic Resources, Technical University of Munich, Campus for Biotechnology and Sustainability, 94315 Straubing, Germany, Fraunhofer IGB, Branch BioCat, 94315 Straubing, Germany, Catalysis Research Center, Technical University of Munich, 85748 Garching, Germany, The University of Queensland, School of Chemistry and Molecular Biosciences, 68 Cooper Road, St. Lucia 4072, Australia
Methods: sugar analysis, GPC, fermentation, media composition, preculture preparation, UHPLC-UV-ESI-MS/MS, crude glycerol analysis
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12. Compound ID: 2013
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, cell wall polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_144144,IEDB_144825,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 619
Aucken HM, Wilkinson SG, Pitt TL "Re-evaluation of the serotypes of Serratia marcescens and separation into two schemes based on lipopolysaccharide (O) and capsular polysaccharide (K) antigens" -
Microbiology 144 (1998) 639-653
Chemical and serological analysis has revealed that many of the 29 O serotype reference strains of Serratia marcescens contain both neutral and acidic polysaccharides which correspond to LPS O antigens and capsular K antigens, respectively. New O and K antigen typing schemes have therefore been devised, based on the known chemical structures of the surface polysaccharides of the organism. These schemes were designed to allow the specific detection of these antigens on unknown strains using ELISAs. O antigens were detected using whole cells cultured in broth then autoclaved to remove capsular material, while K antigens were detected using formolized whole cells which had been cultured on glycerol agar to enhance capsule production. After testing with the 29 reference strains as well as 423 distinct clinical strains, it was apparent that different aspects of chemical structure were associated with different degrees of serological reactivity and the typing schemes were modified further to accommodate this. In general, the O antigen repeating unit structures were chemically simple with di- or trisaccharide backbones. Serological specificity was often provided solely by the presence or absence of an O-acetyl substituent, or a change in the linkage between two sugar residues. Five of the O serotypes in the new scheme were represented by 12 of the 29 reference strains, while three reference strains lacked O antigens altogether, resulting in the elimination of 10 of the original O types. In contrast, the K antigen repeating unit structures were more complex and chemically diverse, having at least four sugar residues. Three K types were each seen in two reference strains while 12 of the 29 reference strains were acapsular. Thus, the resulting schemes contain 19 O types and 14 K types and allow the definitive serotype identification of S. marcescens.
Lipopolysaccharide, antigen, LPS, structure, K-antigen, O-antigen, capsular polysaccharide, Serratia marcescens, Serratia, serotyping, O-serotype
NCBI PubMed ID: 9534235Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: haucken@phls.co.uk
Institutions: Laboratory of Hospital Infection, Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University, Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, chromatography, Quellung reaction, serum adsorption assays
- Article ID: 815
Holst O, Aucken HM, Seltmann G "Structural and serological characterization of the O-specific polysaccharide of the lipopolysaccharide from proposed new serotype O29 of Serratia marcescens" -
Journal of Endotoxin Research 4(3) (1997) 215-220
The structure of the repeating unit of the O-antigenic polysaccharide from the lipopolysaccharide (LPS) of Serratia marcescens strain 111 was determined by compositional and methylation analyses and NMR spectroscopy as →6)-a-D-Glcp-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→ (Rha, rhamnose) which represents a new O-antigenic structure in LPS of S. marcescens but is similar to the structure of the repeating unit of the O-antigen of S. marcescens 018: →6)-a-D-GlcpNAc-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→. (Oxiey D., Wilkinson S.G. Structure of a neutral polymer isolated from the lipopolysaccharide of the reference strain for S. marcescens serogroup 018. Carbohydrate Research 1989; 195: 111-115). Serological investigations using S. marcescens 0- and K-specific ELISA tests and immunoblotting showed that S111 reacted with anti-018 and anti-K4 sera, and that the anti-S111 serum reacted with serotype strain 018. The K4 reaction was confirmed as capsular by the Quellung reaction. After absorption with the heterologous strain, S. marcescens 018 and strain 111 were shown to be immunologically distinct, probably because of the presence of the GlcNAc residue in 018. We propose to add S111 to the O-serotype strains of S. marcescens as 029.
Lipopolysaccharide, LPS, structural, characterization, polysaccharide, serotype, O-specific, O-specific polysaccharide, serological, Serratia marcescens, Serratia
Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: oholst@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Laboratory of Hospital Infection, Public Health Laboratory Service, London, UK, Robert-Koch-lnstitut, Bundesinstitut fur Infektionskrankheiten und nicht ubertragbare Krankheiten, Bereich Wernigerode, Wernigerode, Germany
Methods: NMR-2D, methylation, GLC-MS
- Article ID: 4999
Hashimoto M, Satou R, Ozono M, Inagawa H, Soma GI "Characterization of the O-antigen polysaccharide derived from Pantoea agglomerans IG1 lipopolysaccharide" -
Carbohydrate Research 449 (2017) 32-36
A polysaccharide fraction was isolated from the Pantoea agglomerans IG1 lipopolysaccharide (IP-PA1), and its O-antigenic polysaccharide was characterized by chemical analyses and 1D and 2D 1H and 13C NMR spectroscopy. The polysaccharide is composed of linear tetrasaccharide repeating units, consisting of glucose and rhamnose, where 40% of one of the rhamnose residues is substituted with glucose: →2)-α-l-Rhap-(1→6)-α-d-Glcp-(1→2)-[β-d-Glcp-(1→3)]0.4-α-l-Rhap-(1→2)-α-l-Rhap-(1→.
Lipopolysaccharide, O-antigenic polysaccharide, NMR spectroscopy, Pantoea agglomerans, Wheat symbiotic bacteria
NCBI PubMed ID: 28686930Publication DOI: 10.1016/j.carres.2017.06.017Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: hassy@eng.kagoshima-u.ac.jp
Institutions: Department of Chemistry, Biotechnology, and Chemical Engineering, Kagoshima University, Kagoshima, Japan, Faculty of Medicine, Kagawa University, Miki-cho, Kita-gun, Kagawa, Japan, Research Institute for Healthy Living, Niigata University of Pharmacy and Applied Life Sciences, Akiba-ku, Niigata, Japan, Control of Innate Immunity TRA, Bio-Lab, Kagawa, Japan
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GC-MS, sugar analysis, dephosphorylation, 31P NMR, acid hydrolysis
- Article ID: 5229
Vinogradov E, Sadovskaya I, Grard T, Murphy J, Mahony J, Chapot-Chartier MP, van Sinderen D "Structural studies of the cell wall polysaccharide from Lactococcus lactis UC509.9" -
Carbohydrate Research 461 (2018) 25-31
Lactococcus lactis is the most widely utilised starter bacterial species in dairy fermentations. The L. lactis cell envelope contains polysaccharides, which, among other known functions, serve as bacteriophage receptors. Our previous studies have highlighted the structural diversity of these so-called cell wall polysaccharides (CWPSs) among L. lactis strains that could account for the narrow host range of most lactococcal bacteriophages. In the present work, we studied the CWPS of L. lactis strain UC509.9, an Irish dairy starter strain that is host to the temperate and well-characterized P335-type phage Tuc2009. The UC509.9 CWPS structure was analyzed by methylation, deacetylation/deamination, Smith degradation and 2D NMR spectroscopy. The CWPS consists of a linear backbone composed of a tetrasaccharide repeat unit, partially substituted with a branched phosphorylated oligosaccharide having a common trisaccharide and three non-stoichiometric substitutions.
structure, NMR spectroscopy, Lactococcus lactis, Cell-wall polysaccharide
NCBI PubMed ID: 29573584Publication DOI: 10.1016/j.carres.2018.03.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca; D. van Sinderen
Institutions: School of Microbiology, University College Cork, Cork, Ireland, Micalis Institute, INRA, AgroParisTech, Université Paris-Saclay, Jouy-en-Josas, France, National Research Council, 100 Sussex Dr, Ottawa K1A0R6, Canada, Univ. Littoral Cote d'Opale, Convention ANSES, EA 7394, ICV Charles Violette, Univ. Lille, Univ. Artois, INRA, ISA F-62321, Boulogne-sur-mer, France
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, deacylation, acid hydrolysis, anion-exchange chromatography, Smith degradation, deamination, HPLC, GPC
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13. Compound ID: 2529
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a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-4)-+ P-2)-+ a-Kdop-(2-4)-+ P-4)-+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(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-(1-P
| |
P-6)-+ P-4)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 861
Knirel YA, Bystrova OV, Shashkov AS, Kocharova NA, Senchenkova SN, Moll H, Lindner B, Zähringer U, Hatano K, Pier GB "Structural analysis of the lipopolysaccharide core of a rough, cystic fibrosis isolate of Pseudomonas aeruginosa" -
European Journal of Biochemistry 268(17) (2001) 4708-4719
Lipopolysaccharide (LPS) expressed by isolates of Pseudomonas aeruginosa from cystic fibrosis patients lacks the O-polysaccharide chain but the degree to which the rest of the molecule changes has not been determined. We analyzed, for the first time, the core structure of an LPS from a rough, cystic fibrosis isolate of P. aeruginosa. The products of mild acid hydrolysis and strong alkaline degradation of the LPS were studied by ESI MS, MALDI MS, and NMR spectroscopy. The following structure was determined for the highest-phosphorylated core-lipid A backbone oligosaccharide isolated after alkaline deacylation of the LPS: [structure: see text] where Kdo and Hep are 3-deoxy-D-manno-octulosonic acid and L-glycero-D-manno-heptose, respectively; all sugars are in the pyranose form and have the D configuration unless stated otherwise. The outer core region occurs as two isomeric glycoforms differing in the position of rhamnose (Rha). The inner core region carries four phosphorylation sites at two Hep residues, HepI being predominantly bisphosphorylated and HepII monophosphorylated. In the intact LPS, both Hep residues carry monophosphate and diphosphate groups in nonstoichiometric quantities, GalN is N-acylated by an L-alanyl group, HepII is 7-O-carbamoylated, and the outer core region is nonstoichiometrically O-acetylated at four sites. Therefore, the switch to the LPS-rough phenotype in cystic fibrosis isolates of P. aeruginosa is not accompanied by losses of core monosaccharide, phosphate or acyl components. The exact positions of the O-acetyl groups and the role of the previously undescribed O-acetylation in the LPS core of P. aeruginosa remain to be determined.
Lipopolysaccharide, structure, core, isolate, structural, analysis, structural analysis, Pseudomonas, Pseudomonas aeruginosa, lipopolysaccharide core, rough, site, location, phosphorylation, cystic fibrosis
NCBI PubMed ID: 11532007Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, ESI-MS, mild acid hydrolysis, alkaline degradation
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14. Compound ID: 2530
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a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-4)-+ P-2)-+ a-Kdop-(2-4)-+ P-4)-+
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a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpNAc-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-a-D-GlcpNAc-(1-P
| |
P-6)-+ P-4)-+ |
Show graphically |
Structure type: oligomer
Trivial name: N-acetylated core-lipid A backbone
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130659,IEDB_135394,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_140088,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150077,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885822,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 861
Knirel YA, Bystrova OV, Shashkov AS, Kocharova NA, Senchenkova SN, Moll H, Lindner B, Zähringer U, Hatano K, Pier GB "Structural analysis of the lipopolysaccharide core of a rough, cystic fibrosis isolate of Pseudomonas aeruginosa" -
European Journal of Biochemistry 268(17) (2001) 4708-4719
Lipopolysaccharide (LPS) expressed by isolates of Pseudomonas aeruginosa from cystic fibrosis patients lacks the O-polysaccharide chain but the degree to which the rest of the molecule changes has not been determined. We analyzed, for the first time, the core structure of an LPS from a rough, cystic fibrosis isolate of P. aeruginosa. The products of mild acid hydrolysis and strong alkaline degradation of the LPS were studied by ESI MS, MALDI MS, and NMR spectroscopy. The following structure was determined for the highest-phosphorylated core-lipid A backbone oligosaccharide isolated after alkaline deacylation of the LPS: [structure: see text] where Kdo and Hep are 3-deoxy-D-manno-octulosonic acid and L-glycero-D-manno-heptose, respectively; all sugars are in the pyranose form and have the D configuration unless stated otherwise. The outer core region occurs as two isomeric glycoforms differing in the position of rhamnose (Rha). The inner core region carries four phosphorylation sites at two Hep residues, HepI being predominantly bisphosphorylated and HepII monophosphorylated. In the intact LPS, both Hep residues carry monophosphate and diphosphate groups in nonstoichiometric quantities, GalN is N-acylated by an L-alanyl group, HepII is 7-O-carbamoylated, and the outer core region is nonstoichiometrically O-acetylated at four sites. Therefore, the switch to the LPS-rough phenotype in cystic fibrosis isolates of P. aeruginosa is not accompanied by losses of core monosaccharide, phosphate or acyl components. The exact positions of the O-acetyl groups and the role of the previously undescribed O-acetylation in the LPS core of P. aeruginosa remain to be determined.
Lipopolysaccharide, structure, core, isolate, structural, analysis, structural analysis, Pseudomonas, Pseudomonas aeruginosa, lipopolysaccharide core, rough, site, location, phosphorylation, cystic fibrosis
NCBI PubMed ID: 11532007Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, ESI-MS, mild acid hydrolysis, alkaline degradation
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15. Compound ID: 2532
|
a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-4)-+ a-Kdop-(2-4)-+
| | |
a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpNAc-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-a-D-GlcpNAc-(1-P |
Show graphically |
Structure type: oligomer
Trivial name: N-acetylated core-lipid A backbone
Compound class: core + lipid A
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130659,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_140088,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144144,IEDB_144998,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_2189047,IEDB_225177,IEDB_885822,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 861
Knirel YA, Bystrova OV, Shashkov AS, Kocharova NA, Senchenkova SN, Moll H, Lindner B, Zähringer U, Hatano K, Pier GB "Structural analysis of the lipopolysaccharide core of a rough, cystic fibrosis isolate of Pseudomonas aeruginosa" -
European Journal of Biochemistry 268(17) (2001) 4708-4719
Lipopolysaccharide (LPS) expressed by isolates of Pseudomonas aeruginosa from cystic fibrosis patients lacks the O-polysaccharide chain but the degree to which the rest of the molecule changes has not been determined. We analyzed, for the first time, the core structure of an LPS from a rough, cystic fibrosis isolate of P. aeruginosa. The products of mild acid hydrolysis and strong alkaline degradation of the LPS were studied by ESI MS, MALDI MS, and NMR spectroscopy. The following structure was determined for the highest-phosphorylated core-lipid A backbone oligosaccharide isolated after alkaline deacylation of the LPS: [structure: see text] where Kdo and Hep are 3-deoxy-D-manno-octulosonic acid and L-glycero-D-manno-heptose, respectively; all sugars are in the pyranose form and have the D configuration unless stated otherwise. The outer core region occurs as two isomeric glycoforms differing in the position of rhamnose (Rha). The inner core region carries four phosphorylation sites at two Hep residues, HepI being predominantly bisphosphorylated and HepII monophosphorylated. In the intact LPS, both Hep residues carry monophosphate and diphosphate groups in nonstoichiometric quantities, GalN is N-acylated by an L-alanyl group, HepII is 7-O-carbamoylated, and the outer core region is nonstoichiometrically O-acetylated at four sites. Therefore, the switch to the LPS-rough phenotype in cystic fibrosis isolates of P. aeruginosa is not accompanied by losses of core monosaccharide, phosphate or acyl components. The exact positions of the O-acetyl groups and the role of the previously undescribed O-acetylation in the LPS core of P. aeruginosa remain to be determined.
Lipopolysaccharide, structure, core, isolate, structural, analysis, structural analysis, Pseudomonas, Pseudomonas aeruginosa, lipopolysaccharide core, rough, site, location, phosphorylation, cystic fibrosis
NCBI PubMed ID: 11532007Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, ESI-MS, mild acid hydrolysis, alkaline degradation
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