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1. Compound ID: 336
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R-3HOBut-(1-2)-+ a-D-Glcp-(1-6)-+
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-6)-a-D-GlcpN3(30%)Ac-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-2)-a-D-Glcp-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Grosskurth H, Dabrowski J "Reinvestigation of the O-specific polysaccharides of Hafnia alvei lipopolysaccharides isolated from strains ATCC 13337 and 1187" -
Carbohydrate Research 307(1-2) (1998) 173-176
The structure of the O-specific polysaccharides of the lipopolysaccharides produced by Hafnia alvei strains ATCC 13337 and 1187 was reinvestigated. The position of phosphate group in the repeating units of the polysaccharides was established with the aid of 1H detected, 31P edited NMR spectra. According to the results obtained, the polysaccharides are teichoic acid-like polymers with the repeating units of the following structure: [formula: see text] where Acyl = D-3-hydroxylbutyryl, and 3-O-acetylation was approximately 30%
Lipopolysaccharide, O-specific polysaccharide, Hafnia alvei
NCBI PubMed ID: 9658571Publication DOI: 10.1016/S0008-6215(98)00035-4Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: NMR-2D, methylation, FAB-MS, NMR, sugar analysis, Smith degradation
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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2. Compound ID: 337
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R-3HOBut-(1-2)-+
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-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 94
Gamian A, Katzenellenbogen E, Romanowska E, Grosskurth H, Dabrowski J "Reinvestigation of the O-specific polysaccharides of Hafnia alvei lipopolysaccharides isolated from strains ATCC 13337 and 1187" -
Carbohydrate Research 307(1-2) (1998) 173-176
The structure of the O-specific polysaccharides of the lipopolysaccharides produced by Hafnia alvei strains ATCC 13337 and 1187 was reinvestigated. The position of phosphate group in the repeating units of the polysaccharides was established with the aid of 1H detected, 31P edited NMR spectra. According to the results obtained, the polysaccharides are teichoic acid-like polymers with the repeating units of the following structure: [formula: see text] where Acyl = D-3-hydroxylbutyryl, and 3-O-acetylation was approximately 30%
Lipopolysaccharide, O-specific polysaccharide, Hafnia alvei
NCBI PubMed ID: 9658571Publication DOI: 10.1016/S0008-6215(98)00035-4Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: NMR-2D, methylation, FAB-MS, NMR, sugar analysis, Smith degradation
- Article ID: 3364
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- Article ID: 3485
Katzenellenbogen E, Kocharova NA, Korzeniowska-Kowal A, Gamian A, Bogulska M, Szostko B, Shashkov AS, Knirel YA "Immunochemical studies of the lipopolysaccharides of Hafnia alvei PCM 1219 and other strains with the O-antigens containing D-glucose 1-phosphate and 2-deoxy-2-[(R)-3-hydroxybutyramido]-D-glucose" -
Archivum Immunologiae et Therapiae Experimentalis 56(5) (2008) 347-352
INTRODUCTION: Hafnia alveiis the only species of the genus Hafnia, which belongs to the family of Enterobacteriaceae. These Gram-negative bacteria are commonly distributed in the natural environment and are often the cause of human opportunistic infections. Their lipopolysaccharides (LPSs) are important surface antigens which are responsible for the serological specificity and numerous cross-reactions with other enterobacterial genera. So far, 29 different O-polysaccharide (OPS, O-antigen) structures in Hafnias LPSs have been established and for some of them the molecular basis of the serological activity has been elucidated. MATERIALS AND METHODS: OPS from H. alvei strain PCM 1219 was obtained by mild acid hydrolysis of the LPS followed by gel permeation chromatography of carbohydrate material on Sephadex G-50 column. The polysaccharide structure was determined using chemical methods as well as (13)C NMR and (1)H NMR spectroscopy. For serological studies, SDS-PAGE, immunoblotting, and passive hemagglutination tests were used. RESULTS: The serological studies revealed a cross-reactivity of the LPSs of H. alvei PCM 1219 and a group of H. alvei strains with an O-antigen containing D-glucose 1-phosphate and [(R)-3-hydroxybutyramido]-D-glucose. The following structure of the OPS was established: where Acyl stands for (R)-3-hydroxybutyryl and the degree of O-acetylation is ~70%. The structure of the core oligosaccharide was found to be typical of the genus Hafnia. CONCLUSIONS: Based on the OPS structure and serological results it was concluded that H. alvei strain PCM 1219 should be classified in the same serogroup as the H. alvei type strain ATCC 13337 and five other strains containing D-glucose 1-phosphate and 2-deoxy-2-[(R)-3-hydroxybutyramido]-D-glucose in their O-antigens.
O-antigen, Hafnia alvei, enterobacteria, bacterial polysaccharide structure, Serological cross-reactivity
NCBI PubMed ID: 18836891Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: katzenel@iitd.pan.wroc.pl
Institutions: Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Weigla 12, 53-114, Wroclaw, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, GC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
- Article ID: 4328
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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3. Compound ID: 408
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-4)-a-D-GalpA-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-2)-b-D-GalpA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_153207,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 138
Uhrin D, Chandan V, Altman E "Structural characterization of the O-chain polysaccharide from Proteus mirabilis strain 7570" -
Canadian Journal of Chemistry 73 (1995) 1600-1604
The O-chain polysaccharide produced by Proteus mirabilis strain 7570 was shown by chemical analysis and ID and 2D NMR spectroscopy to be a high molecular weight acidic linear polymer of tetrasaccha-ride repeating units, composed of D-galacturonic acid, 2-acetamido-2-deoxy-D-galactose, and 2-acetamido-2-deoxy-D-glucose (2:1:1). In addition, native O-chain was randomly substituted by O-acetyl groups.
Lipopolysaccharide, NMR, LPS, structure, strain, structural, characterization, polysaccharide, Proteus, Proteus mirabilis, O-chain
Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON KlA OR6, Canada, Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava, Slovakia.
Methods: 13C NMR, 1H NMR, methylation, carbodiimide reduction
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4. Compound ID: 727
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R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
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-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-6)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, CPS
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_147450,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_742248,IEDB_885822,SB_163,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 193
Vinogradov EV, Pantophlet R, Dijkshoorn L, Brade L, Holst O, Brade H "Structural and serological characterisation of two O-specific polysaccharides of Acinetobacter" -
European Journal of Biochemistry 239 (1996) 602-610
Extraction of dry bacteria of Acinetobacter strain 34 (DNA group 2) or Acinetobacter strain 108 (DNA group 13) by phenol/water yielded a polymer that was identified by means of serological studies and fatty acid analysis as S-form lipopolysaccharide. Degradation of the lipopolysaccharides of strains 34 and 108 in 1% acetic acid and 5% acetic acid, respectively, and gel-permeation chromatography gave the respective O-antigenic polysaccharides, the structures of which were determined, by compositional analysis and NMR spectroscopy of the polysaccharide, as [Sequence: see text] for strain 108, where D-Fucp3NBuOH represents 3-[(R)-3-hydroxybutyramido] -3,6-dideoxy-D-galactose and D-GalpANAc represents 2-acetamido-2-deoxy-D-galacturonic acid. Both structures were specifically recognised in Western blots by polyclonal rabbit antisera and there was no cross-reaction between these two structures.
Lipopolysaccharide, NMR, Acinetobacter, serology, Western blot
NCBI PubMed ID: 8774703Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Department of Medical Microbiology, Leiden University Hospital, Leiden, The Netherlands
Methods: NMR-2D, NMR, composition analysis
- Article ID: 680
Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O2 containing 3,6-dideoxy-3-N-(D-3-hydroxybutyryl)amino-D-galactose" -
European Journal of Biochemistry 233 (1995) 899-906
A polysaccharide containing D-galactose, 2-deoxy-2-N-acetylamino-D-galactose and 3,6-dideoxy-3-N-(D-3-hydroxybutyryl)amino-D-galactose, probably corresponding to the lipopolysaccharide side chain, was obtained from an aqueous phenol extract of isolated cell walls from Acinetobacter baumannii strain O2. By means of NMR studies and chemical degradations, the repeating unit of the polymer was identified as a branched hexasaccharide of the structure shown, where Fuc3N represents 3-amino-3,6-dideoxygalactose and R represents D-3-hydroxybutyryl. Serological tests indicated that the polymer corresponded to the O2 antigen.
Lipopolysaccharide, Acinetobacter, Acinetobacter baumannii, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-amino-3, 3-hydroxybutyric acid
NCBI PubMed ID: 8521857Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: School of Chemistry, University of Hull, England.
Methods: NMR-2D, methylation, partial acid hydrolysis, NMR, Smith degradation
- Article ID: 4328
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4533
Hu D, Liu B, Dijkshoorn L, Wang L, Reeves PR "Diversity in the major polysaccharide antigen of Acinetobacter baumannii assessed by DNA sequencing, and development of a molecular serotyping scheme" -
PLoS One 8(7) (2013) e70329
We have sequenced the gene clusters for type strains of the Acinetobacter baumannii serotyping scheme developed in the 1990s, and used the sequences to better understand diversity in surface polysaccharides of the genus. We obtained genome sequences for 27 available serovar type strains, and identified 25 polysaccharide gene cluster sequences. There are structures for 12 of these polysaccharides, and in general the genes present are appropriate to the structure where known. This greatly facilitates interpretation. We also find 53 different glycosyltransferase genes, and for 7 strains can provisionally allocate specific genes to all linkages. We identified primers that will distinguish the 25 sequence forms by PCR or microarray, or alternatively the genes can be used to determine serotype by 'molecular serology'. We applied the latter to 190 Acinetobacter genome-derived gene-clusters, and found 76 that have one of the 25 gene-cluster forms. We also found novel gene clusters and added 52 new gene-cluster sequence forms with different wzy genes and different gene contents. Altogether, the strains that have one of the original 25 sequence forms include 98 A. baumannii (24 from our strains) and 5 A. nosocomialis (3 from our strains), whereas 32 genomes from 12 species other than A. baumannii or A. nosocomialis, all have new sequence forms. One of the 25 serovar type sequences is found to be in European clone I (EC I), 2 are in EC II but none in EC III. The public genome strains add an additional 52 new sequence forms, and also bring the number found in EC I to 5, in EC II to 9 and in EC III to 2.
antigen, structure, Acinetobacter baumannii, gene cluster, glycosyltransferase, serotyping, genome, surface polysaccharide, polysaccharide antigen
NCBI PubMed ID: 23922982Publication DOI: 10.1371/journal.pone.0070329Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Peter R. Reeves
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, Department of Infectious Diseases, Leiden University Medical Center, Leiden, The Netherlands, School of Molecular Bioscience, University of Sydney, Sydney, Australia
Methods: PCR, DNA sequencing, DNA techniques, genetic metods
- 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
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5. Compound ID: 729
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R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
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-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-3)-D-Gro-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 193
Vinogradov EV, Pantophlet R, Dijkshoorn L, Brade L, Holst O, Brade H "Structural and serological characterisation of two O-specific polysaccharides of Acinetobacter" -
European Journal of Biochemistry 239 (1996) 602-610
Extraction of dry bacteria of Acinetobacter strain 34 (DNA group 2) or Acinetobacter strain 108 (DNA group 13) by phenol/water yielded a polymer that was identified by means of serological studies and fatty acid analysis as S-form lipopolysaccharide. Degradation of the lipopolysaccharides of strains 34 and 108 in 1% acetic acid and 5% acetic acid, respectively, and gel-permeation chromatography gave the respective O-antigenic polysaccharides, the structures of which were determined, by compositional analysis and NMR spectroscopy of the polysaccharide, as [Sequence: see text] for strain 108, where D-Fucp3NBuOH represents 3-[(R)-3-hydroxybutyramido] -3,6-dideoxy-D-galactose and D-GalpANAc represents 2-acetamido-2-deoxy-D-galacturonic acid. Both structures were specifically recognised in Western blots by polyclonal rabbit antisera and there was no cross-reaction between these two structures.
Lipopolysaccharide, NMR, Acinetobacter, serology, Western blot
NCBI PubMed ID: 8774703Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Department of Medical Microbiology, Leiden University Hospital, Leiden, The Netherlands
Methods: NMR-2D, NMR, composition analysis
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6. Compound ID: 883
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a-D-GalpNAc-(1-3)-+
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-3)-b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-4)-b-D-GlcpA-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_140630,IEDB_141501,IEDB_141582,IEDB_141584,IEDB_153207,IEDB_153510,IEDB_153749,IEDB_423153,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 248
Gwozdzinski K, Pieniazek A, Kaca W "Lipopolysaccharide from Proteus mirabilis O29 induces changes in red blood cell membrane lipids and proteins" -
International Journal of Biochemistry and Cell Biology 35(3) (2003) 333-338
Alterations in red blood cell (RBC) plasma membranes, i.e. in lipids and proteins, and osmotic fragility of these cells after treatment with Proteus mirabilis O29 endotoxin (lipolysaccharide (LPS)) were examined using a spin labelling method. At the highest concentration of LPS, insignificantly decreased fluidity of membrane lipids was observed. Changes in conformation of membrane proteins were determined by two covalently bound spin labels, 4-maleimido-2,2,6,6-tetramethylpiperidine- 1-oxyl (MSL) and 4-iodoacetamido-2,2,6,6-tetramethylpiperidine-1-oxyl (ISL). The analysis of spectra of MSL and ISL showed modifications in membrane proteins in red blood cells treated with the highest concentration of lipopolysaccharide. On the other hand, in the case of isolated membranes, disturbances in membrane were observed for all concentrations of LPS. The alterations in membrane lipids and proteins are paralleled in a significant rise in osmotic fragility of RBCs upon endotoxin treatment. These results provide experimental evidence that P. mirabilis O29 LPS causes deleterious changes in membranes of human red blood cells. They show that action of lipopolysaccharide mainly concerns the membrane cytoskeleton
Lipopolysaccharide, conformation, LPS, blood, human, analysis, cell, molecular, lipid, protein, endotoxin, Proteus, Proteus mirabilis, biophysics, modification, method, treatment, action, alteration, blood cells, bound, case, Cell Membrane, cells, change, concentration, experimental, fluidity, lipids, membrane, Membrane Lipids, Membrane Proteins, membranes, osmotic, plasma, proteins, red blood cells
NCBI PubMed ID: 12531246Journal NLM ID: 9508482Publisher: Amsterdam: Elsevier
Correspondence: kgwozdz@biol.uni.lodz.pl
Institutions: Department of Molecular Biophysics, University of Lodz, Polish Academy of Sciences, 90-237, Lodz, Poland, Institute of Microbiology, University of Lodz, Polish Academy of Sciences, 90-237 Lodz, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, 90-237 Lodz, Poland
- Article ID: 493
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 875
Kocharova NA, Maszewska A, Zatonsky GV, Bystrova OV, Ziolkowski A, Torzewska A, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-polysaccharide of Providencia alcalifaciens O21 containing 3-formamido-3,6-dideoxy-D-galactose" -
Carbohydrate Research 338(13) (2003) 1425-1430
The O-polysaccharide (O-antigen) of Providencia alcalifaciens O21 was obtained by mild acid degradation of the lipopolysaccharide and studied by chemical methods and NMR spectroscopy. It was found that the polysaccharide is built up of branched pentasaccharide repeating units with a terminal residue of 3-formamido-3,6-dideoxy-D-galactose (D-Fuc3NFo) and has the following structure: [structure: see text]. Anti-P. alcalifaciens O21 serum cross-reacted with the O-antigen of Proteus vulgaris O47, which contains a GalNAc trisaccharide similar to that present in the P. alcalifaciens O21 O-polysaccharide.
structure, polysaccharide, acid, O-polysaccharide, O polysaccharide, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens
NCBI PubMed ID: 12801716Publication DOI: 10.1016/S0008-6215(03)00178-2Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Methods: methylation, NMR, acid hydrolysis, N-deformylation/N-trideuterioacetylation
- Article ID: 1093
Perepelov AV, Shashkov AS, Babicka D, Senchenkova SN, Bartodziejska B, Rozalski A, Knirel YA "Structure of the O-specific polysaccharide of the bacterium Proteus vulgaris O23" -
Biochemistry (Moscow) 65(9) (2000) 1055-1059
An O-specific polysaccharide was obtained by mild acid degradation of P. mirabilis O29 lipopolysaccharide (LPS) and found to contain 2-acetamido-2-deoxy-D-galactose and D-glucuronic acid (D-GlcA) in the ratio 3:1. Studies of the polysaccharide by 1H- and 13C NMR spectroscopy including two-dimensional correlation spectroscopy (COSY), total correlation spectroscopy (TOCSY), nuclear Overhauser effect spectroscopy (NOESY), and H-detected 1H,13C-heteronuclear multiple-quantum coherence (HMQC) experiments demonstrated the following structure of the branched tetrasaccharide repeating unit:
O-antigen; lipopolysaccharide; bacterial polysaccharide; structure; Proteus mirabilis
NCBI PubMed ID: 10713543Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, 117913 Moscow, Leninsk Prospekt 47, Microbiology and Virology Ceter, PAN, Lodz, Poland, Institute of Mcrobiology and Immunology, University of Lodz, Poland
Methods: NMR-2D, NMR, sugar analysis
- Article ID: 1094
Perepelov AV, Shashkov AS, Senchenkova SN, Knirel YA, Literacka E, Kaca W "Structure of the O-specific polysaccharide of the bacterium Proteus mirabilis O29" -
Biochemistry (Moscow) 65(2) (2000) 176-179
An O-specific polysaccharide was obtained by mild acid degradation of P. mirabilis O29 lipopolysaccharide (LPS) and found to contain 2-acetamido-2-deoxy-D-galactose and D-glucuronic acid (D-GlcA) in the ratio 3:1. Studies fo the polysaccharide by 1H- and 13C NMR spectroscopy including two-dimensional correlation spectroscopy (COSY), total correlation spectroscopy (TOCSY), nuclear Overhauser effect spectroscopy (NOESY), and H-detected 1H,13C-heteronuclear multiple-quantum coherence (HMQC) experiments demonstrated the following structure of the branched tetrasaccharide repeating unit: (see formula in text).
Lipopolysaccharide, LPS, structure, strain, structural, characterization, polysaccharide, O-antigen, bacteria, O-specific, O-specific polysaccharide, Proteus, Proteus mirabilis, serological, chemical, immunochemical
NCBI PubMed ID: 10713543Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: perepel@ioc.ac.ru
Institutions: Institute of Microbiology and Immunology, University of Lodz, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodz, Poland, N.D. Zelinsky Institute of Organic Chamisry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991 Russia
Methods: NMR-2D, NMR, sugar analysis, determination of absolute configuration
- Article ID: 1466
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 1552
Perepelov AV, Zablotni A, Shashkov AS, Knirel YA, Sidorczyk Z "Structure of the O-polysaccharide and serological studies of the lipopolysaccharide of Proteus mirabilis 2002" -
Carbohydrate Research 340 (2005) 2305-2310
The structure of the O-polysaccharide of the lipopolysaccharide of Proteus mirabilis 2002 was elucidated by chemical methods and (1)H and (13)C NMR spectroscopy. It was found that the polysaccharide consists of branched pentasaccharide repeating units having the following structure: The O-polysaccharide of P. mirabilis 2002 has a common tetrasaccharide fragment with that of P. mirabilis 52/57 from serogroup O29, and the lipopolysaccharides of the two strains are serologically related. Therefore, based on the structural and serological data, we propose to classify P. mirabilis 2002 into the Proteus O29 serogroup as a subgroup O29a,29b.
Lipopolysaccharide, structure, polysaccharide, O-polysaccharide, O polysaccharide, O-specific, O-specific polysaccharide, Proteus, Proteus mirabilis, serological, serogroup, classification, preparation, genomospecies
NCBI PubMed ID: 16084933Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland
Methods: methylation, NMR, sugar analysis
- Article ID: 4801
Siwinska M, Levina EA, Ovchinnikova OG, Drzewiecka D, Shashkov AS, Rozalski A, Knirel YA "Classification of a Proteus penneri clinical isolate with a unique O-antigen structure to a new Proteus serogroup, O80" -
Carbohydrate Research 407 (2015) 131-136
Proteus penneri is an opportunistic pathogen, which may cause severe diseases, most frequently urinary tract infections in immunocompromised patients. P. penneri Br 114 exhibiting a good swarming growth ability as an S-form strain was isolated from a wound of a patient in Lodz, Poland. Serological studies using ELISA and Western blotting and chemical analyses along with (1)H and (13)C NMR spectroscopy showed that the O-antigen (O-polysaccharide) of this strain is unique among the known Proteus serotypes O1-O79. It possesses a linear pentasaccharide repeating unit containing a partially O-acetylated amide of D-glucuronic acid (GlcA) with L-serine having the following structure: [structure: see text]. These data are a basis for creating a new Proteus serogroup, O80, so far represented by the single Br 114 isolate. The O80 is the 21st O-serogroup containing P. penneri strains and the fourth serogroup based on Proteus spp. clinical isolates from Lodz, Poland.
Lipopolysaccharide, O-antigen, Proteus penneri, serological classification, bacterial polysaccharide structure
NCBI PubMed ID: 25771295Publication DOI: 10.1016/j.carres.2015.02.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: domkam@biol.uni.lodz.pl
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, 90-237 Łódź, Poland, Higher Chemical College of the Russian Academy of Sciences, 125047 Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, 90-237 Łódź, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, ELISA, GLC, mild acid hydrolysis, Western blotting, de-O-acetylation, composition analysis, GPC
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7. Compound ID: 930
|
S-3HOBut-(1-2)-+
|
-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 269
Jankowski S, Rowinski S, Cisowska A, Gamian A "The sensitivity of Hafnia alvei strains to the bactericidal effect of serum" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 59-64
Most Hafnia alvei strains are sensitive to the bactericidal action of normal bovine serum (NBS) as well as to a serum in which the alternative pathway of complement activation has been thermally blocked. Introduction of polysaccharides (PS) to NBS lowers the bactericidal effect. In a serum in which the alternative pathway of complement activation is blocked, PS completely cancels the bacterial effect.
strain, polysaccharide, Hafnia alvei, Hafnia, sensitivity, serum, bactericidal, effect, serum killing
NCBI PubMed ID: 8821399Journal NLM ID: 9315554Publisher: Elsevier
Institutions: Department of Microbiology, Academy of Medicine, Chalubinskiego 4, 50-368 Wroclaw, Poland, Ludwik Hirschfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Czerska 6, 53-114 Wroclaw, Poland.
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8. Compound ID: 942
|
Cho-(1--P--6)--+
|
-6)-b-D-Glcp-(1-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-1)-D-Rib-ol-(5-P- |
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Structure type: polymer chemical repeating unit
Trivial name: common antigen
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114703,IEDB_115009,IEDB_116046,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_140624,IEDB_141109,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_241118,IEDB_591403,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 283
Karlsson C, Jansson P, Sorensen UBS "The pneumococcal common antigen C-polysaccharide occurs in different forms - Mono-substituted or di-substituted with phosphocholine" -
European Journal of Biochemistry 265(3) (1999) 1091-1097
The structure of the pneumococcal common antigen, C-polysaccharide, from a noncapsulated pneumococcal strain, CSR SCS2, was studied using 1H NMR, 13C NMR and 31P NMR spectroscopy. The dependence of NMR chemical shifts on the variation in pD was also studied. It was established that the C-polysaccharide is composed of a backbone of tetrasaccharide-ribitol repeating units that are linked to each other by a phosphodiester linkage between position 5 of a D-ribitol residue and position 6 of a β-D-glucopyranosyl residue. The polysaccharide is substituted with one residue of phosphocholine at position 6 of the 4-substituted 2-acetamido-2-deoxy-α-D-galactopyranosyl residue. Both galactosamine residues in the polysaccharide are N-acetylated. O)-P-Cho | 6 6)-β-D-Glcp-(1→3)-α-AATp-(1→4)-α-D-GalpNAc-(1→3)-β-D-GalpNAc-(1→1)-D-ribitol-5-P-(O→ where AAT is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose and Cho is choline. This structure differs, concerning phosphocholine substituents and N-acetylation, from those reported previously for pneumococcal C-polysaccharide [Jennings, H.J., Lugowski, C. & Young, N.M. (1980) Biochemistry 19, 4712-4719; Fischer, W., Behr, T., Hartmann, R., Peter-Katalinic, J. & Egge, H. (1993) Eur. J. Biochem. 215, 851-857; Kulakowska, M., Brisson, J.-R., Griffith, D.W., Young, N.M. & Jennings, H.J. (1993) Can. J. Chem. 71, 644-648]. The structures of the C-polysaccharides present in three pneumococcal types were also examined. They contain one (in 18B) or two (in 32F and 32A) phosphocholine residues in the repeating unit. The degree of substitution was not determined. The backbone of all examined C-polysaccharides was identical and in all cases both galactosamine residues appeared to be N-acetylated.
Streptococcus pneumoniae, capsular polysaccharide, common antigen, Phosphocholine, pneumococcal, C-polysaccharide
NCBI PubMed ID: 10518806Publication DOI: 10.1046/j.1432-1327.1999.00835.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Pererik.jansson@kfcmail.hs.sll.se
Institutions: Clinical Research Centre, Karolinska Institute, Huddinge University Hospital, Novum Huddinge, Sweden, Department of Medical Microbiology and Immunology, University of Aarhus, Denmark.
Methods: 13C NMR, 1H NMR, ELISA, 31P NMR
- Article ID: 4827
Geno KA, Gilbert GL, Song JY, Skovsted IC, Klugman KP, Jones C, Konradsen HB, Nahm MH "Pneumococcal Capsules and Their Types: Past, Present, and Future" -
Clinical Microbiology Reviews 28(3) (2015) 871-899
Streptococcus pneumoniae (the pneumococcus) is an important human pathogen. Its virulence is largely due to its polysaccharide capsule, which shields it from the host immune system, and because of this, the capsule has been extensively studied. Studies of the capsule led to the identification of DNA as the genetic material, identification of many different capsular serotypes, and identification of the serotype-specific nature of protection by adaptive immunity. Recent studies have led to the determination of capsular polysaccharide structures for many serotypes using advanced analytical technologies, complete elucidation of genetic basis for the capsular types, and the development of highly effective pneumococcal conjugate vaccines. Conjugate vaccine use has altered the serotype distribution by either serotype replacement or switching, and this has increased the need to serotype pneumococci. Due to great advances in molecular technologies and our understanding of the pneumococcal genome, molecular approaches have become powerful tools to predict pneumococcal serotypes. In addition, more-precise and -efficient serotyping methods that directly detect polysaccharide structures are emerging. These improvements in our capabilities will greatly enhance future investigations of pneumococcal epidemiology and diseases and the biology of colonization and innate immunity to pneumococcal capsules.
serotype, Streptococcus pneumoniae, vaccines, Pneumococcal Capsules
NCBI PubMed ID: 26085553Publication DOI: 10.1128/CMR.00024-15Journal NLM ID: 8807282Publisher: Washington, DC: American Society for Microbiology
Correspondence: Moon H. Nahm
Institutions: Department of Pathology, University of Alabama at Birmingham, Birmingham, Alabama, USA, Centre for Infectious Diseases and Microbiology, Institute of Clinical Pathology & Medical Research, Westmead Hospital, Wentworthville, New South Wales, Australia, Marie Bashir Institute for Infectious Diseases and Biosecurity, University of Sydney, Sydney, New South Wales, Australia, Division of Infectious Disease, Department of Internal Medicine, Korea University Guro Hospital, Seoul, South Korea, SSI Diagnostica, Division of Microbiology and Diagnostics, Statens Serum Institut, Copenhagen, Denmark, Pneumonia Program Strategy Team, Bill & Melinda Gates Foundation, Seattle, Washington, USA, Laboratory for Molecular Structure, NIBSC, South Mimms, Herts, United Kingdom, Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama, USA
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9. Compound ID: 983
|
S-3HOBut-(1-2)-+
|
-2)-a-D-Glcp-(1--P--6)--a-D-GlcpN3(30%)Ac-(1-4)-a-D-GalpNAc6Ac-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 269
Jankowski S, Rowinski S, Cisowska A, Gamian A "The sensitivity of Hafnia alvei strains to the bactericidal effect of serum" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 59-64
Most Hafnia alvei strains are sensitive to the bactericidal action of normal bovine serum (NBS) as well as to a serum in which the alternative pathway of complement activation has been thermally blocked. Introduction of polysaccharides (PS) to NBS lowers the bactericidal effect. In a serum in which the alternative pathway of complement activation is blocked, PS completely cancels the bacterial effect.
strain, polysaccharide, Hafnia alvei, Hafnia, sensitivity, serum, bactericidal, effect, serum killing
NCBI PubMed ID: 8821399Journal NLM ID: 9315554Publisher: Elsevier
Institutions: Department of Microbiology, Academy of Medicine, Chalubinskiego 4, 50-368 Wroclaw, Poland, Ludwik Hirschfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Czerska 6, 53-114 Wroclaw, Poland.
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10. Compound ID: 1216
|
a-iYerp7Ac-(1-4)-+
|
-3)-b-D-GalpNAc-(1-3)-a-D-GalpNAc-(1-
iYer = 3,6-dideoxy-4-C-[(R)-1-acetoxyethyl]-D-xylo-hexose (1'-O-acetylyersiniose B, 1'-O-acetylisoyersiniose) |
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Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_153207,IEDB_2218588,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 380
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: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
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11. Compound ID: 1236
|
a-Colp-(1-2)-b-Yerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
Yer = 3,6-dideoxy-4-C-[(S)-1-hydroxyethyl]-D-xylo-hexose (yersiniose A) |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 380
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: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- Article ID: 4005
Cunneen MM, Pacinelli E, Song WC, Reeves PR "Genetic analysis of the O-antigen gene clusters of Yersinia pseudotuberculosis O:6 and O:7" -
Glycobiology 21(9) (2011) 1140-1146
Among the 21 O-polysaccharide (OPS) O-antigen based serotypes described for Yersinia pseudotuberculosis, those of O:6 and O:7 are unusual in that both contain colitose (4-keto-3,6 dideoxy-D-mannose or 4-keto-3,6-dideoxy-L-xylo-hexose), which has not otherwise been reported for this species, and the O:6 OPS also contains yersiniose A (4-C[(R)-1-hydroxyethyl]-3,6,dideoxy-D-xylo-hexose), another unusual dideoxyhexose sugar. In Y. pseudotuberculosis the genes for OPS synthesis generally cluster together between the hemH and gsk loci. Here we present the sequences of the OPS gene clusters of Y. pseudotuberculosis O:6 and O:7, and the location of the genes required for synthesis of these OPSs, except that there is still ambiguity regarding allocation of some of the glycosyltransferase functions. The O:6 and O:7 gene clusters have much in common with each other, but differ substantially from the group of 13 gene clusters already sequenced, which share several features and sequence similarities. We also present a possible sequence of events for the derivation of the O:6 and O:7 gene clusters from the most closely related of the set of 13 sequenced previously.
Yersinia pseudotuberculosis, O-antigen gene cluster
NCBI PubMed ID: 21325338Publication DOI: 10.1093/glycob/cwr010Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia
Methods: genetic methods
- Article ID: 4044
Kenyon JJ, De Castro C, Cunneen MM, Reeves PR, Molinaro A, Holst O, Skurnik M "The genetics and structure of the O-specific polysaccharide of Yersinia pseudotuberculosis serotype O:10 and its relationship to Escherichia coli O111 and Salmonella enterica O35" -
Glycobiology 21(9) (2011) 1131-1139
The O-specific polysaccharide (OPS) is a variable constituent of the lipopolysaccharide of Gram-negative bacteria. The polymorphic nature of OPSs within a species is usually first defined serologically, and the current serotyping scheme for Yersinia pseudotuberculosis consists of 21 O serotypes of which 15 have been characterized genetically and structurally. Here, we present the structure and DNA sequence of Y. pseudotuberculosis O:10 OPS. The O unit consists of one residue each of d-galactopyranose, N-acetyl-d-galactosamine (2-amino-2-deoxy-d-galactopyranose) and d-glucopyranose in the backbone, with two colitose (3,6-dideoxy-l-xylo-hexopyranose) side-branch residues. This structure is very similar to that shared by Escherichia coli O111 and Salmonella enterica O35. The gene cluster sequences of these serotypes, however, have only low levels of similarity to that of Y. pseudotuberculosis O:10, although there is significant conservation of gene order. Within Y. pseudotuberculosis, the O10 structure is most closely related to the O:6 and O:7 structures.
O-specific polysaccharide, colitose, Yersinia pseudotuberculosis O:10, Escherichia coli O111, Salmonella enterica O35
NCBI PubMed ID: 21321053Publication DOI: 10.1093/glycob/cwr006Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: P.R. Reeves
; C. De Castro
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia.
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, mild acid hydrolysis
- Article ID: 4328
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 5010
Kenyon JJ, Cunneen MM, Reeves PR "Genetics and evolution of Yersinia pseudotuberculosis O-specific polysaccharides: a novel pattern of O-antigen diversity" -
FEMS Microbiology Reviews 41(2) (2017) 200-217
O-antigen polysaccharide is a major immunogenic feature of the lipopolysaccharide of Gram-negative bacteria, and most species produce a large variety of forms that differ substantially from one another. There are 18 known O-antigen forms in the Yersinia pseudotuberculosis complex, which are typical in being composed of multiple copies of a short oligosaccharide called an O unit. The O-antigen gene clusters are located between the hemH and gsk genes, and are atypical as 15 of them are closely related, each having one of five downstream gene modules for alternative main-chain synthesis, and one of seven upstream modules for alternative side-branch sugar synthesis. As a result, many of the genes are in more than one gene cluster. The gene order in each module is such that, in general, the earlier a gene product functions in O-unit synthesis, the closer the gene is to the 5 end for side-branch modules or the 3 end for main-chain modules. We propose a model whereby natural selection could generate the observed pattern in gene order, a pattern that has also been observed in other species.
Lipopolysaccharide, serotype, O antigen, gene cluster, O-specific polysaccharide, Yersinia pseudotuberculosis, O-antigen polysaccharide
NCBI PubMed ID: 28364730Publication DOI: 10.1093/femsre/fux002Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW 2006, Australia, Institute of Health and Biomedical Innovation, Queensland University of Technology. Brisbane, QLD 4001, Australia
Methods: function analysis of gene clusters
- Article ID: 6089
Knirel YA, Anisimov AP, Kislichkina AA, Kondakova AN, Bystrova OV, Vagaiskaya AS, Shatalin KY, Shashkov AS, Dentovskaya SV "Lipopolysaccharide of the Yersinia pseudotuberculosis Complex" -
Biomolecules 11(10) (2021) 1410
Lipopolysaccharide (LPS), localized in the outer leaflet of the outer membrane, serves as the major surface component of the Gram-negative bacterial cell envelope responsible for the activation of the host's innate immune system. Variations of the LPS structure utilized by Gram-negative bacteria promote survival by providing resistance to components of the innate immune system and preventing recognition by TLR4. This review summarizes studies of the biosynthesis of Yersinia pseudotuberculosis complex LPSs, and the roles of their structural components in molecular mechanisms of yersiniae pathogenesis and immunogenesis.
core, Pathogenesis, lipid A, Yersinia pseudotuberculosis, lipopolysaccharide (LPS), Yersinia pestis, Plague, pathogenicity factor
NCBI PubMed ID: 34680043Publication DOI: 10.3390/biom11101410Journal NLM ID: 101596414Publisher: Basel, Switzerland: MDPI
Correspondence: Y.A. Knirel
; S.V. Dentovskaya
Institutions: Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory for Plague Microbiology, Especially Dangerous Infections Department, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Russia, Department of Biochemistry and Molecular Pharmacology, New York University School of Medicine, New York, NY 10016, USA
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12. Compound ID: 1237
|
a-Colp-(1-2)-+ a-D-Glcp-(1-6)-+
| |
-6)-b-D-Glcp-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 380
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: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1869
Komandrova NA, Gorshkova RP, Zubkov VA, Ovodov YS "The structure of the O-specific polysaccharide chain of the lipopolysaccharide of Yersinia pseudotuberculosis serovar VII" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 15 (1989) 104-110
An O-specific polysaccharide of Yersinia pseudotuberculosis serovar VII has been isolated and characterized. The polysaccharide consists of colitose, D-glucose and 2-acetamido-2-deoxy-D-galactose in the ratio 1 : 2 : 2. From the results of methylation analysis, partial acid hydrolysis, 1H and 13C NMR spectroscopy the structure of the repeating unit of the O-specific polysaccharide is deduced as follows:
NCBI PubMed ID: 2472792Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok
Methods: 13C NMR, 1H NMR
- Article ID: 2681
Ovodov YS, Gorshkova RP, Tomshich SV, Komandrova NA, Zubkov VA, Kalmykova EN, Isakov VV "Chemical and Immunochemical studies on lipopolysaccharides of some Yersinia species - A review of some recent investigations" -
Journal of Carbohydrate Chemistry 11 (1992) 21-35
The present paper revealed the results of some recent chemical and immunochemical studies of the lipopolysaccharides from various species and erologie variants of Yersinia genus as follows: Y. pseudotuberculosis IIC and VII; Y. enterocolitica 0:1, 2a, 3; 0:2a, 2b, 3; 0:3; 0:4, 32; 0:5; 0:5,27; 0:6,31; 0:7,8; 0:19,8; 0:8; Y. frederiksenii 0:16,29; Y. intermedia 0:4,33; Y. aldovae.
Publication DOI: 10.1080/07328309208016139Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: The Pacific Institute of Bioorganic Chemistry, Far East Branch of the USSR Academy of Sciences, 690022, Vladivostok, U.S.S.R
Methods: 13C NMR, 1H NMR
- Article ID: 4328
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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 6089
Knirel YA, Anisimov AP, Kislichkina AA, Kondakova AN, Bystrova OV, Vagaiskaya AS, Shatalin KY, Shashkov AS, Dentovskaya SV "Lipopolysaccharide of the Yersinia pseudotuberculosis Complex" -
Biomolecules 11(10) (2021) 1410
Lipopolysaccharide (LPS), localized in the outer leaflet of the outer membrane, serves as the major surface component of the Gram-negative bacterial cell envelope responsible for the activation of the host's innate immune system. Variations of the LPS structure utilized by Gram-negative bacteria promote survival by providing resistance to components of the innate immune system and preventing recognition by TLR4. This review summarizes studies of the biosynthesis of Yersinia pseudotuberculosis complex LPSs, and the roles of their structural components in molecular mechanisms of yersiniae pathogenesis and immunogenesis.
core, Pathogenesis, lipid A, Yersinia pseudotuberculosis, lipopolysaccharide (LPS), Yersinia pestis, Plague, pathogenicity factor
NCBI PubMed ID: 34680043Publication DOI: 10.3390/biom11101410Journal NLM ID: 101596414Publisher: Basel, Switzerland: MDPI
Correspondence: Y.A. Knirel
; S.V. Dentovskaya
Institutions: Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory for Plague Microbiology, Especially Dangerous Infections Department, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Russia, Department of Biochemistry and Molecular Pharmacology, New York University School of Medicine, New York, NY 10016, USA
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13. Compound ID: 1278
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_136105,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_153207,IEDB_225177,IEDB_885822,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 404
Vinion-Dubiel AD, Goldberg JB "Lipopolysaccharide of Burkholderia cepacia complex" -
Journal of Endotoxin Research 9(4) (2003) 201-213
Burkholderia cepacia complex (Bcc) is a group of phenotypically similar, genetically distinct bacteria that are beneficial to the environment but can also cause severe human infections. Bcc are being exploited for use as bioremediation agents and as a way to combat agricultural plant diseases. However, Bcc can cause lung infections in patients with chronic granulomatous disease or cystic fibrosis often resulting in mortality of these patients. Since it is unclear what bacterial components are necessary for causing human infections, studies of Bcc have focused on identifying putative virulence factors. As in other Gram-negative bacteria, the lipopolysaccharide (LPS) of Bcc induces a strong immune response that can contribute to host cell damage. The unusual structure of Bcc LPS lowers the anionic charge of the Bcc cell surface, which inhibits the binding and subsequent effects of cationic antibiotics. These distinguishing features include the substitution of a Ko for a Kdo residue in the inner core oligosaccharide and Ara4N residues bound to phosphates of the lipid A backbone. The structures of O antigen subunits and the consequent serotypes will also be discussed, with particular reference to the O antigen biosynthetic loci of two Bcc strains.
Lipopolysaccharide, structure, Burkholderia, Burkholderia cepacia, O-antigen, complex, endotoxin, Re
NCBI PubMed ID: 12935351Publication DOI: 10.1177/09680519030090040101Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Microbiology, University of Virginia Health Sciences Center, Charlottesville, VA 22908-0734, USA
- Article ID: 639
Gaur D, Wilkinson SG "Lipopolysaccharide from Burkholderia vietnamiensis strain LMG 6999 contains two polymers identical to those present in the reference strain for Burkholderia cepacia serogroup O4" -
FEMS Microbiology Reviews 295 (1997) 183-188
Lipopolysaccharide was isolated from strain LMG 6999 of Burkholderia vietnamiensis. Degradative and NMR spectroscopic studies established the presence of two polymeric fractions based on the following trisaccharide repeating units: I:[-3)aDGalp(1-3)bDGalp(1-3)[Ac(1-2)]bDGalpN(1-]; II:[-3)[Ac(1-2)]aDGalpN(1-3)[Ac(1-2)]bDGalpN(1-4)aLRhap(1-]. The same polymers have previously been found together in lipopolysaccharide from the reference strain for Burkholderia cepacia serogroup O4 and, individually, in those from B. cepacia serogroups C (I) and A (II).
Lipopolysaccharide, LPS, structure, strain, polysaccharide, Burkholderia, Burkholderia cepacia, polymer, O-specific, O-specific polysaccharide, serogroup, reference, Polymers, Burkholderia vietnamiensis
NCBI PubMed ID: 9418254Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: S.G.Wilkinson@chem.hull.ac.uk
Institutions: School of Chemistry, University of Hull, Hull HU6 7RX, UK
Methods: NMR-2D, methylation, NMR, Smith degradation, GPC
- Article ID: 782
Cox AD, Taylor CJ, Anderson AJ, Perry MB, Wilkinson SG "Structures of the two polymers present in the lipopolysaccharide of Burkholderia_Pseudomonas cepacia serogroup O4" -
European Journal of Biochemistry 231 (1995) 784-789
Like several other strains of Burkholderia_Pseudomonas cepacia, the reference strain for serogroup O4 in the French typing scheme [Heidt, A., Monteil, H. & Richard, C. (1983) J. Clin. Microbiol. 18, 738-740] produces a lipopolysaccharide containing two distinct polymers. Attempts to separate the polymers chromatographically were unsuccessful, but the periodate-resistant major polymer could be isolated by application of the Smith degradation technique to the mixture. By means of chemical and NMR spectroscopic analysis, the following structure could be assigned to the repeating unit of the major polymer: →3)-α-D-Galp-(1→3)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→. The following structure of the repeating unit of the minor polymer was established from similar studies of its degradation product, resulting from the oxidation of L-rhamnose (Rha), and of the original mixture: →3)-α-D-GalpNAc-(1→3)-β-D-GalpNAc-(1→4)-α-L-Rhap-(1→. Individually, the polymers have recently been found in related strains of B. cepacia. The minor polymer was identified as the O-antigen in serotype A of a Canadian typing scheme [Beynon, L. M. & Perry, M. B. (1993) Biochem. Cell Biol. 71, 417-420], and the major polymer in serotype C of a Japanese typing scheme [Paramonov, N. A., Shashkov, A. S., Knirel, Y. A., Soldatkina, M. A. & Zakharova, I. Y. (1994) Bioorg. Khim. 20, 984-993]. In the case of the O4 strain studied here, both polymers were produced under a variety of growth conditions.
Lipopolysaccharide, LPS, structure, Burkholderia, Burkholderia cepacia, O-antigen, Pseudomonas, polymer, serogroup, Polymers, Pseudomonas cepacia
NCBI PubMed ID: 7544286Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada.
Methods: NMR, sugar analysis, Smith degradation
- Article ID: 1723
Beynon LM, Perry MB "Structure of the lipopolysaccharide O-antigen of Pseudomonas cepacia serotype A" -
Biochemistry and Cell Biology 71 (1993) 417-420
Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
- Article ID: 5143
Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" -
Natural Product Reports 35(12) (2018) 1251-1293
Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.
lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism
Publication DOI: 10.1039/C8NP00046HJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Correspondence: charles.gauthier@iaf.inrs.ca
Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
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14. Compound ID: 1355
|
Cho-(1--P--6)--+ Cho-(1--P--6)--+
| |
-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-5)-D-Rib-ol-(1--P--6)--b-D-Glcp-(1-3)-a-D-FucpNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: repeating unit of pneumococcal teichoic and lipoteichoic acids
Contained glycoepitopes: IEDB_114703,IEDB_115009,IEDB_116046,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_140624,IEDB_141109,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_241118,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 429
Yother J, Leopold K, White J, Fischer W "Generation and properties of a Streptococcus pneumoniae mutant which does not require choline or analogs for growth" -
Journal of Bacteriology 180(8) (1998) 2093-2101
A mutant (JY2190) of Streptococcus pneumoniae Rx1 which had acquired the ability to grow in the absence of choline and analogs was isolated. Lipoteichoic acid (LTA) and wall teichoic acid (TA) isolated from the mutant were free of phosphocholine and other phosphorylated amino alcohols. Both polymers showed an unaltered chain structure and, in the case of LTA, an unchanged glycolipid anchor. The cell wall composition was also not altered except that, due to the lack of phosphocholine, the phosphate content of cell walls was half that of the parent strain. Isolated cell walls of the mutant were resistant to hydrolysis by pneumococcal autolysin (N-acetylmuramyl-L-alanine amidase) but were cleaved by the muramidases CPL and cellosyl. The lack of active autolysin in the mutant cells became apparent by impaired cell separation at the end of cell division and by resistance against stationary-phase and penicillin-induced lysis. As a result of the absence of choline in the LTA, pneumococcal surface protein A (PspA) was no longer retained on the cytoplasmic membrane. During growth in the presence of choline, which was incorporated as phosphocholine into LTA and TA, the mutant cells separated normally, did not release PspA, and became penicillin sensitive. However, even under these conditions, they did not lyse in the stationary phase, and they showed poor reactivity with antibody to phosphocholine and an increased release of C-polysaccharide from the cell. In contrast to ethanolamine-grown parent cells (A. Tomasz, Proc. Natl. Acad. Sci. USA 59:86-93, 1968), the choline-free mutant cells retained the capability to undergo genetic transformation but, compared to Rx1, with lower frequency and at an earlier stage of growth. The properties of the mutant could be transferred to the parent strain by DNA of the mutant
Streptococcus pneumoniae, teichoic acid, C polysaccharide, choline, lipoteichoic acid
NCBI PubMed ID: 9555891Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: jyother@uab.edu
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama 35294, Institut Biochemie, Universitat Erlangen-Nurnberg, D-91054 Erlangen, Germany
Methods: GLC, HPLC, immunoblotting, microscopy, periodate oxidation
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15. Compound ID: 1356
|
Subst-(1-4)-+
|
b-D-Glcp-(1-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-5)-D-Rib-ol
Subst = 9-fluorenylmethoxycarbonyl (Fmoc) = SMILES O={1}C(O)OCC1C2=C(C3=C1C=CC=C3)C=CC=C2 |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114703,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_885822,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 429
Yother J, Leopold K, White J, Fischer W "Generation and properties of a Streptococcus pneumoniae mutant which does not require choline or analogs for growth" -
Journal of Bacteriology 180(8) (1998) 2093-2101
A mutant (JY2190) of Streptococcus pneumoniae Rx1 which had acquired the ability to grow in the absence of choline and analogs was isolated. Lipoteichoic acid (LTA) and wall teichoic acid (TA) isolated from the mutant were free of phosphocholine and other phosphorylated amino alcohols. Both polymers showed an unaltered chain structure and, in the case of LTA, an unchanged glycolipid anchor. The cell wall composition was also not altered except that, due to the lack of phosphocholine, the phosphate content of cell walls was half that of the parent strain. Isolated cell walls of the mutant were resistant to hydrolysis by pneumococcal autolysin (N-acetylmuramyl-L-alanine amidase) but were cleaved by the muramidases CPL and cellosyl. The lack of active autolysin in the mutant cells became apparent by impaired cell separation at the end of cell division and by resistance against stationary-phase and penicillin-induced lysis. As a result of the absence of choline in the LTA, pneumococcal surface protein A (PspA) was no longer retained on the cytoplasmic membrane. During growth in the presence of choline, which was incorporated as phosphocholine into LTA and TA, the mutant cells separated normally, did not release PspA, and became penicillin sensitive. However, even under these conditions, they did not lyse in the stationary phase, and they showed poor reactivity with antibody to phosphocholine and an increased release of C-polysaccharide from the cell. In contrast to ethanolamine-grown parent cells (A. Tomasz, Proc. Natl. Acad. Sci. USA 59:86-93, 1968), the choline-free mutant cells retained the capability to undergo genetic transformation but, compared to Rx1, with lower frequency and at an earlier stage of growth. The properties of the mutant could be transferred to the parent strain by DNA of the mutant
Streptococcus pneumoniae, teichoic acid, C polysaccharide, choline, lipoteichoic acid
NCBI PubMed ID: 9555891Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: jyother@uab.edu
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama 35294, Institut Biochemie, Universitat Erlangen-Nurnberg, D-91054 Erlangen, Germany
Methods: GLC, HPLC, immunoblotting, microscopy, periodate oxidation
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