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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130648,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_140108,IEDB_140122,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153214,IEDB_190606,IEDB_885822,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_44,SB_7,SB_72,SB_88

• Article ID: 697
  Hashimoto M, Kirikae F, Dohi T, Kusumoto S, Suda Y, Kirikae T "Structural elucidation of a capsular polysaccharide from a clinical isolate of Bacteroides vulgatus from a patient with Crohn's disease" - European Journal of Biochemistry 268(11) (2001) 3139-3144
  

  The structure of a capsular polysaccharide (CPS) from a clinical isolate of Bacteroides vulgatus was elucidated. B. vulgatus IMCJ 1204 was isolated from feces of a patient with Crohn's disease. CPS was prepared by phenol/water extraction of the bacterial cells followed by hydrophobic interaction chromatography and then gel filtration chromatography of the extract. The structure of CPS was determined by chemical analysis and NMR spectroscopy including DQF-COSY, TOCSY, ROESY, HSQC-TOCSY, HMQC and HMBC to be a polysaccharide composed of the following repeating unit: →3)β-D-Glcp(1→6)[α-D-GalpNAc(1→2)β-D-Galp(1→4)]β-D-GlcpNAc(1→3)α-D-Galp(1→4)β-D-Manp(1→.

  NMR, structure, clinical, disease, isolate, structural, capsular, polysaccharide, capsular polysaccharide, elucidation, Bacteroides, Bacteroides vulgatus

  NCBI PubMed ID: 11389714
  Publication DOI: 10.1046/j.1432-1327.2001.02147.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: tkirikae@ri.imcj.go.jp
  Institutions: Research Institute, International Medical Center of Japan, Tokyo, Japan, Graduate School of Science, Osaka University, Japan
  Methods: NMR-2D, NMR, chemical analysis
  
   
  
  Bacteroides vulgatus IMCJ1204
  CSDB ID 500 (all data & tools)
• 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/B978-0-12-819475-1.00005-5
  Publisher: 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
  
   
  
  Bacteroides vulgatus IMCJ 1204
  CSDB ID 7023 (all data & tools)

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Structure type: polymer chemical repeating unit
Trivial name: the polysaccharide moiety of LPS
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_72

• Article ID: 805
  Hashimoto M, Kirikae F, Dohi T, Adachi S, Kusumoto S, Suda Y, Fujita T, Naoki H, Kirikae T "Structural study on lipid A and the O-specific polysaccharide of the lipopolysaccharide from a clinical isolate of Bacteroides vulgatus from a patient with Crohn's disease" - European Journal of Biochemistry 269(15) (2002) 3715-3721
  

  Bacteroides vulgatus has been shown to be involved in the aggravation of colitis. Previously, we separated two potent virulence factors, capsular polysaccharide (CPS)and lipopolysaccharide (LPS), from a clinical isolate of B. vulgatus and characterized the structure of CPS. In this study, we elucidated the structures of O-antigen polysaccharide (OPS) and lipid A in the LPS. LPS was subjected to weak acid hydrolysis to produce the lipid A fraction and polysaccharide fraction. Lipid A was isolated by preparative TLC, and its structure determined byMS andNMR to be similar to that of Bacteroides fragilis except for the number of fatty acids. The polysaccharide fraction was subjected to gel-filtration chromatography to give an OPS-rich fraction. The structure of OPS was determined by chemical analysis and NMRspectroscopy to be a polysaccharide composed of the following repeating unit: →4)a-L-Rhap(1→3)b-DManp(→.

  Lipopolysaccharide, NMR, Bacteroides vulgatus, fast-atom-bombardment tandem mass spectrometry, MALDITOF-MS

  NCBI PubMed ID: 12153568
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: tkirikae@ri.imcj.go.jp
  Institutions: Graduate School of Science, Osaka University, Japan, Research Institute, International Medical Center of Japan, Department of Oral Microbiology, Asahi University School of Dentistry, Japan, Department of Bacteriology, Hyogo College of Medicine, Japan, Suntory Institute for Bioorganic Research, Japan
  Methods: NMR-2D, SDS-PAGE, MALDI-TOF MS, FAB-MS/MS
  
   
  
  Bacteroides vulgatus IMCJ 1204
  CSDB ID 2401 (all data & tools)
• Article ID: 885
  Komandrova NA, Tomshich SV, Isakov VV, Romanenko LA "Structure of sulfated O-specific polysaccharide of the marine bacterium Pseudoalteromonas marinoglutinosa KMM 232" - Biochemistry (Moscow) 63(10) (1998) 1200-1204
  

  A sulfated O-specific polysaccharide containing D-mannose, L-rhamnose, and the sulfate group was obtained by mild acid hydrolysis of lipopolysaccharide (S-form) of the marine bacterium Pseudoalteromonas marinoglutinosa KMM 232. Based on analysis of methylation and 13C NMR spectroscopy of native and desulfated polysaccharides, the following structure of disaccharide repeat unit in the O-specific polysaccharide has been established: [scheme]. This is the first report of a sulfated O-specific polysaccharide isolated from gram-negative bacteria.

  structure, polysaccharide, NMR spectroscopy, bacteria, O-specific, O-specific polysaccharide, PAGE, marine, Pseudoalteromonas, sulfated

  NCBI PubMed ID: 9864455
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: elnaz@piboc.marine.su
  Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivistok, Russia
  Methods: methylation, NMR, desulfation
  
   
  
  Pseudoalteromonas mariniglutinosa KMM 232
  CSDB ID 3080 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

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

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

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Bacteroides vulgatus
  CSDB ID 27826 (all data & tools)
• Article ID: 5421
  Di Lorenzo F, De Castro C, Silipo A, Molinaro A "Lipopolysaccharide structures of Gram-negative populations in the gut microbiota and effects on host interactions" - FEMS Microbiology Reviews 43(3) (2019) 257-272
  

  The human gastrointestinal tract harbors a heterogeneous and complex microbial community, which plays a key role in human health. The gut microbiota controls the development of the immune system by setting systemic threshold for immune activation. Glycoconjugates, such as lipopolysaccharides, from gut bacteria have been shown to be able to elicit both systemic proinflammatory and immunomodulatory responses. This phenomenon is particularly intriguing considering that the immune system is charged with the task to distinguish the beneficial microbes from the pathogens, even if the commensal bacteria have molecular patterns resembling those of the pathogenic counterparts. Therefore, the importance of the chemical structure of these macromolecules in fine tuning this delicate equilibrium is beyond question. This review offers an overview of the current understanding of chemical peculiarities of the lipopolysaccharides isolated from the gut microbiota, and their relationships to their biological activity in terms of immune system maturation and development.

  innate immunity, Structural characterization, gut immunity, gut microbiota, TLR4/MD-2

  NCBI PubMed ID: 30649292
  Publication DOI: 10.1093/femsre/fuz002
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: flaviana.dilorenzo@unina.it
  Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy, Task Force on Microbiome Studies, University of Naples Federico II, Naples 80126, Italy, Department of Agricultural Sciences, University of Naples Federico II, via Università 100, 80055 Portici, Italy
  
   
  
  Bacteroides vulgatus IMCJ 1204
  CSDB ID 994 (all data & tools)
• Article ID: 5797
  Kokoulin MS, Lizanov IN, Romanenko LA, Chikalovets IV "Structure of phosphorylated and sulfated polysaccharides from lipopolysaccharide of marine bacterium Marinicella litoralis KMM 3900(T)" - Carbohydrate Research 490 (2020) 107961
  

  Two polysaccharide fractions were obtained by mild acid degradation of the lipopolysaccharide of the marine bacterium Marinicella litoralis KMM 3900T. The major polysaccharide was found to contain glycerol 1-phosphate (PGro) and methyl phosphate substituents (PMe), and the following structure of its disaccharide repeating unit was established by sugar analysis, dephosphorylation, Smith degradation, and 1D and 2D NMR spectroscopy: →4)-α-L-Rhap2PGro(~40%)-(1→3)-β-D-Manp6PMe(~80%)-(1 →. The minor polysaccharide was shown to consist of 4-O-sulfate-D-mannopyranosyl residues, non-stoichiometric methylated at O-3 and acetylated at O-6: →2)-α-D-Manp3R4S6Ac(~75%)-(1→, where R is Me (85%) or H (15%).

  Lipopolysaccharide, polysaccharide, Marine bacterium, methyl phosphate, 3-O-Methyl-D-mannose, Marinicella litoralis

  NCBI PubMed ID: 32120020
  Publication DOI: 10.1016/j.carres.2020.107961
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Prospekt 100 let Vladivostoku 159, Vladivostok, 690022, Russia, Far Eastern Federal University, Ul. Sukhanova 8, 690950, Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, 31P NMR, ESI-MS, anion-exchange chromatography, GC, Smith degradation, de-O-acetylation, FTIR, GPC, HF treatment
  
   
  
  Marinicella litoralis KMM 3900(T)
  CSDB ID 32139 (all data & tools)