Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: viilian, NIZO B40
Compound class: EPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_145001,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

• Article ID: 128
  Tuinier R, Zoon P, Olieman C, Stuart MAC, Fleer GJ, De Kruif CG "Isolation and physical characterization of an exocellular polysaccharide" - Biopolymers 49(1) (1999) 1-9
  

  The physical properties of a polysaccharide produced by the lactic acid bacterium Lactococcus lactis subsp. cremoris strain NIZO B40 were investigated. Separation of the polysaccharide from most low molar mass compounds in the culture broth was performed by filtration processes. Residual proteins and peptides were removed by washing with a mixture of formic acid, ethanol, and water. Gel permeation chromatography (GPC) was used to size fractionate the polysaccharide. Fractions were analyzed by multiangle static light scattering in aqueous 0.10 M NaNO3 solutions from which a number- (Mn) and weight-averaged (Mw) molar mass of (1.47 +/- 0.06).10(3) and (1.62 +/- 0.07).10(3) kg/mol, respectively, were calculated so that Mw/Mn approximately 1.13. The number-averaged radius of gyration was found to be 86 +/- 2 nm. From dynamic light scattering an apparent z-averaged diffusion coefficient was obtained. Upon correcting for the contributions from intramolecular modes by extrapolating to zero wave vector a hydrodynamic radius of 86 +/- 4 nm was calculated. Theoretical models for random coil polymers show that this z-averaged hydrodynamic radius is consistent with the z-averaged radius of gyration, 97 +/- 3 nm, as found with GPC.

  characterization, polysaccharide, exocellular, exocellular polysaccharide, physical, isolation, gel permeation chromatography, light scattering

  NCBI PubMed ID: 10070259
  Publication DOI: 10.1002/(SICI)1097-0282(199901)49:1<1::AID-BIP1>3.0.CO;2-B
  Journal NLM ID: 0372525
  Publisher: Wiley Interscience
  Institutions: NIZO food research, P. O. Box 20, 6710 BA Ede, The Netherlands, Laboratory for Physical, Chemistry and Colloid Science, Department of Biomolecular Sciences, Wageningen Agricultural University, Dreijenplein 6, 6703 HB Wageningen, The Netherlands.
  Methods: GPC, light scattering
  
   
  
  Lactococcus lactis ssp. cremoris NIZO B40
  CSDB ID 5242 (all data & tools)
• Article ID: 145
  Van Kranenburg R, Van Swam II, Marugg JD, Kleerebezem M, De Vos WM "Exopolysaccharide biosynthesis in Lactococcus lactis NIZO B40: Functional analysis of the glycosyltransferase genes involved in synthesis of the polysaccharide backbone" - Journal of Bacteriology 181(1) (1999) 338-340
  

  We used homologous and heterologous expression of the glycosyltransferase genes of the Lactococcus lactis NIZO B40 eps gene cluster to determine the activity and substrate specificities of the encoded enzymes and established the order of assembly of the trisaccharide backbone of the exopolysaccharide repeating unit. EpsD links glucose-1-phosphate from UDP-glucose to a lipid carrier, EpsE and EpsF link glucose from UDP-glucose to lipid-linked glucose, and EpsG links galactose from UDP-galactose to lipid-linked cellobiose. Furthermore, EpsJ appeared to be involved in EPS biosynthesis as a galactosyl phosphotransferase or an enzyme which releases the backbone oligosaccharide from the lipid carrier.

  biosynthesis, synthesis, functional, gene, exopolysaccharide, Lactococcus lactis, glycosyltransferase

  NCBI PubMed ID: 9864348
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: kranenbu@nizo.nl
  Institutions: Microbial Ingredients Section, NIZO Food Research, 6710 BA Ede, The Netherlands.
  Methods: genetic methods, biochemical methods
  
   
  
  Lactococcus lactis NIZO B40
  CSDB ID 5270 (all data & tools)
• Article ID: 256
  Higashimura M, Mulder-Bosman BW, Reich R, Iwasaki T, Robijn GW "Solution properties of viilian, the exopolysaccharide from Lactococcus lactis subsp cremoris SBT 0495" - Biopolymers 54(2) (2000) 143-158
  

  The exopolysaccharide (EPS) "viilian" was isolated from a large-batch fermentation of Lactococcus lactis subsp. cremoris SBT 0495. After applying a newly developed purification procedure, pure viilian with a weight-averaged molar mass of 2.64 x 10(3) kg/mol was obtained in a yield of 0.6 g/L culture broth. The native EPS, as well as lower molar mass fractions obtained by sonication of the native polymer, were studied by capillary viscometry and size-exclusion chromatography (SEC) coupled to multiangle laser light scattering detection (MALLS). From the viscosity data at various ionic strengths, we extracted a Mark-Houwink-Kuhn-Sakurada exponent a = 0.79, and a Smidsrod B value of 0.03. By application of the Hearst, Bohdanecky, and Odijk models for stiff polymer coils, in connection to the experimental viscosity data, we established the characteristic ratio to be C(infinity) = 44 and the intrinsic persistence length q(0) = 11.5 nm. The rms radii of gyration predicted from each of the models were in good agreement with the experimental radii (e.g., (1/2)(w) = 162 nm for native viilian in 0.2M NaNO(3)), as determined by SEC-MALLS. In addition, the Odijk model predicts correct ionic strength-linear charge density dependence of the rms radius of gyration. From the combined viscosity and SEC-MALLS experiments we concluded that, in dilute aqueous solutions, viilian behaves as an intermediately stiff, random coil polyelectrolyte system.Copyright 2000 John Wiley & Sons, Inc.

  exopolysaccharide, Lactococcus, Lactococcus lactis subsp cremoris, solution properties, viilian

  NCBI PubMed ID: 10861375
  Journal NLM ID: 0372525
  Publisher: Wiley Interscience
  Institutions: Snow Brand European Research Laboratories B.V., Zernikepark 6, 9747 AN Groningen, The Netherlands.
  Methods: HPSEC-MALLS
  
   
  
  Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 7116 (all data & tools)
• Article ID: 292
  Kleerebezem M, Van Kranenburg R, Tuinier R, Boels IC, Zoon P, Looijesteijn E, Hugenholtz J, De Vos WM "Exopolysaccharides produced by Lactococcus lactis: from genetic engineering to improved rheological properties?" - Antonie van Leeuwenhoek 76(1) (1999) 357-365
  

  Over the last years, important advances have been made in the study of the production of exopolysaccharides (EPS) by several lactyl bacteria, including Lactococcus lactis. From different EPS-producing lactococcal strains the specific eps gene clusters have been characterised. They contain eps genes, which are involved in EPS repeating unit synthesis, export, polymerisation, and chain length determination. The function of the glycosyltransferase genes has been established and the availability of these genes opened the way to EPS engineering. In addition to the eps genes, biosynthesis of EPS requires a number of housekeeping genes that are involved in the metabolic pathways leading to the EPS-building blocks, the nucleotide sugars. The identification and characterisation of several of these housekeeping genes (galE, galU, rfbABCD) allows the design of metabolic engineering strategies that should lead to increased EPS production levels by L. lactis. Finally, model development has been initiated in order to predict the physicochemical consequences of the addition of a EPS to a product.

  rheological, exopolysaccharides, Lactococcus lactis, Lactococcus, genetic engineering

  NCBI PubMed ID: 10532391
  Journal NLM ID: 0372625
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Wageningen Centre for Food Sciences, NIZO food research, Microbial Ingredients Section and Fermented Products Section, P.O. Box 20, 6710 BA Ede, The Netherlands, Present address: University of Utrecht, Van't Hoff Laboratory for Physical and Colloid Chemistry, Utrecht, The Netherlands.
  
   
  
  Lactococcus lactis B40
  CSDB ID 7408 (all data & tools)
• Article ID: 342
  Oba T, Doesburg KK, Iwasaki T, Sikkema J "Identification of biosynthetic intermediates of the extracellular polysaccharide viilian in Lactococcus lactis subspecies cremoris SBT 0495" - Archives of Microbiology 171(5) (1999) 343-349
  

  Abstract Lactococcus lactis subspecies cremoris SBT 0495 produces the phosphopolysaccharide viilian, which consists of the repeating unit g-d-glucosyl-(1M4)-(f-l-rhamnosyl-(1M2))-(f-d-galactose-1-phosphoryl-(M3)-g-galactosyl-(1M4)-g-d-glucose. A lipid extract was prepared from cells in the late exponential phase of growth and was hydrolyzed by hydrochloric acid under mild conditions to split lipid-linked intermediates in the extract into lipid and sugar moieties. Both moieties were purified by chromatographic techniques and were characterized to identify intermediates of the viilian biosynthetic pathway. A polyisoprenoid isolated from the chloroform-soluble fraction of the hydrolyzed lipid extract was identified by mass spectrometry as undecaprenol. Saccharides isolated from the water-soluble fraction of the hydrolyzed lipid extract by anion-exchange chromatography, were characterized by glycosidic linkage analysis to discriminate sugar moieties of intermediates of viilian biosynthesis from compounds liberated from cell wall components. Some oligosaccharide analogues contain a glycerol residue, suggesting that these are fragments of glycosylglycerides and/or lipoteichoic acid. Three fragments were identified to be glucose, galactosyl-(1M4)-glucose, and rhamnosyl-(1M2)-galactosyl-(1M4)-glucose, which are in agreement with the structure of the repeating unit of viilian. These saccharides most likely represent the first three steps of the sequential assembly of the repeating unit of the undecaprenol assembly

  biosynthesis, polysaccharide, extracellular polysaccharide, Lactococcus lactis, viilian, lipid-linked intermediate

  NCBI PubMed ID: 10382265
  Journal NLM ID: 0410427
  Publisher: Berlin, New York: Springer
  Correspondence: jdx06735@nifty.ne.jp
  Institutions: Snow Brand European Research Laboratories B.V., Zernikepark 6, 9747 AN Groningen, The Netherlands, Sapporo Research Laboratory, Snow Brand Milk Products Co., Ltd., 6-1-1, Naebo-cho, Higashi-ku, Sapporo 065-0043, Japan, Technical Research Institute, Snow Brand Milk Products Co., Ltd., 1-1-2, Minamidai, Kawagoe, Saitama 350-1165, Japan, Research & Development, Friesland Coberco Dairy Foods, P.O. Box 226, 8901 MA Leeuwarden, The Netherlands
  
   
  
  Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 7766 (all data & tools)
• Article ID: 401
  Van Casteren WHM, Dijkema C, Schols HA, Beldman G, Voragen AGJ "Characterisation and modification of the exopolysaccharide produced by Lactobacillus lactis subsp. cremori B40" - Carbohydrate Polymers 37(2) (1999) 123-130
  

  The chemical structure of an exopolysaccharide produced by Lactococcus lactis subsp. cremoris B40 is studied, explaining earlier reported analytical discrepancies. The EPS was found to have a molecular mass of 6.8Ч105 g mol-1 and a molar ratio of rhamnose:galactose:glucose:phosphorus of 1:1.3:2:1.1. NMR indicated that a single phosphate group is present as a phosphodiester. EPS B40 was chemically modified using 0.6 H2SO4, 28 HF or 2 NaOH. From these modifications it could be concluded that galactose 1-phosphate was linked at the 3-position of 1,2,3,4-linked galactose in the backbone of the EPS. Furthermore, it appeared that during the hydrolysis step of the sugar composition analysis the galactose 3-phosphate linkages were only partially split and that, as a result, the amount of galactose was underestimated in presence of phosphate. Finally, it was demonstrated that a crude cellulase preparation was able to degrade dephosphorylated and partially de-rhamnosylated EPS.

  exopolysaccharide, chemical structure, modification, Lactococcus, Lactobacillus, phosphorus

  Publication DOI: 10.1016/S0144-8617(98)00044-7
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Institutions: Wageningen Agricultural University, Department of Food Technology and Nutritional Sciences, Food Science Group, Bomenweg 2, 6703 HD Wageningen, The Netherlands, Wageningen Agricultural University, Department of Biomolecular Sciences, Laboratory of Molecular Physics, Dreijenlaan 3, 6703 HA Wageningen, The Netherlands
  Methods: 13C NMR, 1H NMR, sugar analysis, 31P NMR, acid hydrolysis, alkaline degradation, HPAEC, enzymatic degradation, HPSEC, HF treatment
  
   
  
  Lactococcus lactis ssp. cremoris B40, Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 8394 (all data & tools)
• Article ID: 1376
  Boels IC, Ramos A, Kleerebezem M, De Vos WM "Functional analysis of the Lactococcus lactis galU and galE genes and their impact on sugar nucleotide and exopolysaccharide biosynthesis" - Applied and Environmental Microbiology 67(7) (2001) 3033-3040
  

  biosynthesis, functional, gene, analysis, exopolysaccharide, sugar, Lactococcus lactis, Lactococcus, galE, galU, sugar nucleotide, impact

  Journal NLM ID: 7605801
  Publisher: American Society for Microbiology
  Correspondence: kleerebe@nizo.nl
  Institutions: Department of Flavor and Natural Ingredients,The Netherlands
  
   
  
  Lactococcus lactis MG1363
  CSDB ID 6268 (all data & tools)
• Article ID: 3405
  Gorska S, Grycko P, Rybka J, Gamian A "Exopolysaccharides of lactic acid bacteria: structure and biosynthesis" - Postȩpy Higieny i Medycyny Doświadczalnej [Polish] 61 (2007) 805-818
  

  The group of lactic acid bacteria (LABs) includes four genera: Lactobacillus, Leuconostoc, Pediococcus, and Streptococcus. The most characteristic feature of this group of microorganisms is the production of lactic acid as a main product of carbohydrate metabolism. LABs are responsible for the fermentation of alimentary products and they also produce a variety of agents, among them exopolysaccharides (EPSs), which inhibit the growth of pathogenic bacteria. In this article on the different types of EPSs produced by LABs, data concerning their structure and biosynthesis are presented

  biosynthesis, structure, Streptococcus, Lactic acid bacteria, exopolysaccharides, Lactococcus, Lactobacillus, Leuconostoc

  NCBI PubMed ID: 18097339
  Journal NLM ID: 0421052
  Publisher: Warszawa: Panstwowy Zaklad Wydawnictw Lekarskich
  Institutions: Laboratorium Mikrobiologii Lekarskiej, Instytut Immunologii i Terapii Doswiadczalnej PAN im. L. Hirszfelda we Wroclawiu
  
   
  
  Lactococcus lactis ssp. cremoris
  CSDB ID 21995 (all data & tools)
• Article ID: 4169
  Nakajima H, Hirota T, Toba T, Itoh T, Adachi S "Structure of the extracellular polysaccharide from slime-forming Lactococcus lactis subsp. cremoris SBT 0495" - Carbohydrate Research 224 (1992) 245-253
  

  The extracellular polysaccharide obtained from slime-forming Lactococcus lactis subsp. cremoris SBT 0495 is composed of D-glucose, D-galactose, L-rhamnose, and phosphate. Methylation analysis of the native and dephosphorylated polysaccharides provided information on the linkage of the sugar residues and the location of the phosphate group. N.m.r. spectroscopy confirmed the structure of the polysaccharide, which is assigned the following repeating-unit: [formula: see text]

  NCBI PubMed ID: 1591765
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Technical Research Institute, Snow Brand Milk Products Co., Ltd., Kawagoe, Japan
  
   
  
  Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 116485 (all data & tools)
• Article ID: 5533
  Zhou Y, Cui Y, Qu X "Exopolysaccharides of lactic acid bacteria: Structure, bioactivity and associations: A review" - Carbohydrate Polymers 207 (2019) 317-332
  

  The ability to exhibit various bioactivities is widespread in exopolysaccharide (EPS) of lactic acid bacteria (LAB), and it has been admittedly associated with large structural variability of these polymers. Exceptional bioactivities such as cholesterol-lowering, immunomodulating, antioxidant, antiviral and anticoagulant effects render these biopolymers vast commercial value for global market and application potentials in medicine sector. Therefore, an elaborate understanding of structure-to-function associations will be prerequisite to search natural and artificial EPSs for new applications in functional food, health and medicine fields. In this review, it is presented a significant overview of the latest advances in the field of EPS from genes to application. This review emphasized in the general biosynthesis pathway together with genetic modules, multiple structures, functions, and respective functional mechanisms of LAB-derived EPSs, and the relationships between their structure and bioactivity, which will help to exploit new bioactive drugs from LAB-derived EPS.

  biosynthesis, structure, exopolysaccharide, mechanism, bioactivity, Structure-to-function association

  NCBI PubMed ID: 30600013
  Publication DOI: 10.1016/j.carbpol.2018.11.093
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Correspondence: Y. Cui
  Institutions: Department of Food Science and Engineering, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, China, Institute of Microbiology, Heilongjiang Academy of Sciences, Harbin, China
  
   
  
  Lactococcus lactis ssp. cremoris ARH74, Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 2672 (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
  
   
  
  Lactococcus lactis ssp. cremoris SBT 0495, Lactococcus lactis ssp. cremoris B40, Lactococcus lactis ssp. cremoris ARH53, Lactococcus lactis ssp. cremoris ARH74, Lactococcus lactis ssp. cremoris ARH84, Lactococcus lactis ssp. cremoris ARH87, Lactococcus lactis ssp. cremoris B30, Lactococcus lactis ssp. cremoris NCC 2771 (NIZO B40)
  CSDB ID 25035 (all data & tools)
• Article ID: 5880
  De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" - Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
  

  carbohydrates, polysaccharides, Lactic acid bacteria, exopolysaccharides, glycolipids, glycoproteins, Glycomics

  Publication DOI: 10.1016/B978-044451967-2/00129-X
  Publisher: Elsevier
  Correspondence: ldvuyst@vub.ac.be
  Editors: Barchi J, Kamerling H
  Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
  
   
  
  Lactococcus lactis ssp. cremoris AHR 53, Lactococcus lactis ssp. cremoris NIZO B40, Lactococcus lactis ssp. cremoris SBT 0495
  CSDB ID 25152 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_134624,IEDB_135394,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_742246,IEDB_918313,SB_163,SB_7,SB_87

• Article ID: 189
  Vinogradov E, Korenevsky A, Beveridge TJ "The structure of the rough-type lipopolysaccharide from Shewanella oneidensis MR-1, containing 8-amino-8-deoxy-Kdo and an open-chain form of 2-acetamido-2-deoxy-D-galactose" - Carbohydrate Research 338(19) (2003) 1991-1997
  

  The LPS from Shewanella oneidensis strain MR-1 was analysed by chemical methods and by NMR spectroscopy and mass spectrometry. The LPS contained no polysaccharide O-chain, and its carbohydrate backbone had the following structure: (1S)-GalNAco-(1→4,6)-α-Gal-(1→6)-α-Gal-(1→3)-α-Gal-(1-P-3)-α-DDHep-(1→5)-α-8-aminoKdo4R-(2→6)-β-GlcN4P-(1→6)-α-GlcN1P, where R is P or xXEtNPP. There are several novel aspects to this LPS. It contains a novel linking unit between the core polysaccharide and lipid A moieties, namely 8-amino-3,8-dideoxy-D-manno-octulosonic acid (8-aminoKdo) and a residue of 2-acetamido-2-deoxy-D-galactose (N-acetylgalactosamine, GalNAco) in an open-chain form, linked as cyclic acetal to O-4 and O-6 of D-galactopyranose. The structure contains a phosphodiester linkage between the α-D-galactopyranose and D-glycero-D-manno-heptose (DDHep) residues.

  LPS, core, Kdo, Shewanella

  NCBI PubMed ID: 14499575
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
  Institutions: Institute for Biological Sciences, National Research Council (NRC), 100 Sussex Dr., Ottawa ON K1A 0R6 Canada, Department of Microbiology, College of Biological Science, University of Guelph, Guelph ON N1G 2W1 Canada
  Methods: NMR-2D, NMR, chemical methods
  
   
  
  Shewanella oneidensis MR-1
  CSDB ID 5520 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115013,IEDB_120354,IEDB_123890,IEDB_130645,IEDB_134624,IEDB_135394,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_742246,IEDB_918313,SB_163,SB_7,SB_87

• Article ID: 189
  Vinogradov E, Korenevsky A, Beveridge TJ "The structure of the rough-type lipopolysaccharide from Shewanella oneidensis MR-1, containing 8-amino-8-deoxy-Kdo and an open-chain form of 2-acetamido-2-deoxy-D-galactose" - Carbohydrate Research 338(19) (2003) 1991-1997
  

  The LPS from Shewanella oneidensis strain MR-1 was analysed by chemical methods and by NMR spectroscopy and mass spectrometry. The LPS contained no polysaccharide O-chain, and its carbohydrate backbone had the following structure: (1S)-GalNAco-(1→4,6)-α-Gal-(1→6)-α-Gal-(1→3)-α-Gal-(1-P-3)-α-DDHep-(1→5)-α-8-aminoKdo4R-(2→6)-β-GlcN4P-(1→6)-α-GlcN1P, where R is P or xXEtNPP. There are several novel aspects to this LPS. It contains a novel linking unit between the core polysaccharide and lipid A moieties, namely 8-amino-3,8-dideoxy-D-manno-octulosonic acid (8-aminoKdo) and a residue of 2-acetamido-2-deoxy-D-galactose (N-acetylgalactosamine, GalNAco) in an open-chain form, linked as cyclic acetal to O-4 and O-6 of D-galactopyranose. The structure contains a phosphodiester linkage between the α-D-galactopyranose and D-glycero-D-manno-heptose (DDHep) residues.

  LPS, core, Kdo, Shewanella

  NCBI PubMed ID: 14499575
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
  Institutions: Institute for Biological Sciences, National Research Council (NRC), 100 Sussex Dr., Ottawa ON K1A 0R6 Canada, Department of Microbiology, College of Biological Science, University of Guelph, Guelph ON N1G 2W1 Canada
  Methods: NMR-2D, NMR, chemical methods
  
   
  
  Shewanella oneidensis MR-1
  CSDB ID 5684 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7

• Article ID: 251
  Hansson J, Garegg PJ, Oscarson S "Syntheses of anomerically phosphodiester-linked oligomers of the repeating units of the Haemophilus influenzae types c and f capsular polysaccharides" - Journal of Organic Chemistry 66(19) (2001) 6234-6243
  

  Spacer-equipped dimers and trimers of the repeating units of the capsular polysaccharide of Haemophilus influenzae type c, -4)-3-O-Ac-β-d-GlcpNAc-(1→3)-α-d-Galp-(1-OPO3−, and type f, −3)-β-d-GalpNAc-(1→4)-3-O-Ac-α-d-GalpNAc-(1-OPO3-, have been synthesized for use in immunological studies. H-Phosphonate chemistry was used for the formation of the interglycosidic phosphate diester linkages. Two types of building blocks, a spacer glycoside disaccharide starting monomer (15 and 22) and an anomeric monoester α-H-phosphonate disaccharide elongating monomer (12 and 27), were built up for each serotype structure from properly protected monosaccharide precursors using mainly thioglycosides as glycosyl donors. Stereospecificity in the formation of the α-linked monoester H-phosphonate was possible in type c through crystallization of the pure α-anomer of the precursor hemiacetal from an α/β-mixture, whereas in type f, the hemiacetal was isolated directly as exclusively the α-anomer. Subsequent phosphonylation using triimidazolylphosphine was performed without anomerization. Formation of the anomeric phosphate diester linkages was performed using pivaloyl chloride as coupling reagent followed by I(2)/H(2)O oxidation of the formed diester H-phosphonates. Original experiments afforded no diester product at all, but optimization of the oxidation conditions (lowering the temperature and dilution with pyridine prior to I(2) addition) gave the dimers in good yields (71% and 81%) and, subsequently, after removal of a temporary silyl protecting group in the dimers, the trimers in fair yields (36% and 37%), accompanied by hydrolysis of the dimer phosphate linkage. One-step deprotection through catalytic hydrogenolysis efficiently afforded the target dimer (30 and 36) and trimer structures (32 and 39). The synthetic scheme allows for further elongation to give higher oligomers

  Haemophilus influenzae, capsular polysaccharide, polysaccharides, chemical structure, oligomers, Post-translational modification

  NCBI PubMed ID: 11559168
  Publication DOI: 10.1021/jo001302m
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
  
   
  
  Haemophilus influenzae c
  CSDB ID 6897 (all data & tools)
• Article ID: 264
  Hoog C, Laaksonen A, Widmalm G "Molecular dynamics simulations of the phosphodiester-linked repeating units of the Haemophilus influenzae types c and f capsular polysaccharides" - Journal of Physical Chemistry B 105(29) (2001) 7074-7079
  

  The three-dimensional structure of the repeating units of Haemophilus influenzae types c and f capsular polysaccharides (CPS) have been investigated by molecular dynamics simulations. The models consist of disaccharides joined by phosphodiester linkages, explicit water, and sodium as the counterion. Four 1 ns simulations were performed for each type, with either different starting conformations or different methods to handle long-range truncation effects, namely, Ewald summation or force shift truncation. For the average properties investigated, the choice of the method did not make any significant difference. Limited flexibility was observed close to the sugar residues, whereas at the phosphorus atom, the torsions showed major transitions. For comparison, 3./n,p was measured on CPS material. On the basis of these spin-spin couplings, only small changes are required in the models of the disaccharide repeating unit to agree with data on the CPS. In addition, hydrogen bonding and radial and spatial distribution functions were analyzed to obtain a picture of solvent ordering around the disaccharides.

  Haemophilus, Haemophilus influenzae, capsular polysaccharides, polysaccharides, type, molecular dynamics, simulation

  Publication DOI: 10.1021/jp0041555
  Journal NLM ID: 101157530
  Publisher: Washington, DC: American Chemical Society
  Correspondence: G. Widmalm
  Institutions: Department of Organic Chemistry and Division of Physical Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
  Methods: 1H NMR, 31P NMR
  
   
  
  Haemophilus influenzae c
  CSDB ID 7139 (all data & tools)
• Article ID: 4430
  Ovodov YS "Bacterial capsular antigens. Structural patterns of capsular antigens" - Biochemistry (Moscow) 71(9) (2006) 937-954
  

  Structural patterns of bacterial capsular antigens including capsular polysaccharides and exoglycans are given in this review. In addition, the immunological activity of capsular antigens and their role in type specificity of bacteria are discussed.

  structure, capsular polysaccharides, bacterial capsular antigens, bacterial exoglycans, immunological activity, type specificity

  NCBI PubMed ID: 17009947
  Publication DOI: 10.1134/S000629790609001X
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: ovoys@physiol.komisc.ru
  Institutions: Institute of Physiology, Komi Science Center, Urals Branch of the Russian Academy of Sciences, Syktyvkar 167982, Russia
  
   
  
  Haemophilus influenzae c
  CSDB ID 28777 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_120354,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7

• Article ID: 251
  Hansson J, Garegg PJ, Oscarson S "Syntheses of anomerically phosphodiester-linked oligomers of the repeating units of the Haemophilus influenzae types c and f capsular polysaccharides" - Journal of Organic Chemistry 66(19) (2001) 6234-6243
  

  Spacer-equipped dimers and trimers of the repeating units of the capsular polysaccharide of Haemophilus influenzae type c, -4)-3-O-Ac-β-d-GlcpNAc-(1→3)-α-d-Galp-(1-OPO3−, and type f, −3)-β-d-GalpNAc-(1→4)-3-O-Ac-α-d-GalpNAc-(1-OPO3-, have been synthesized for use in immunological studies. H-Phosphonate chemistry was used for the formation of the interglycosidic phosphate diester linkages. Two types of building blocks, a spacer glycoside disaccharide starting monomer (15 and 22) and an anomeric monoester α-H-phosphonate disaccharide elongating monomer (12 and 27), were built up for each serotype structure from properly protected monosaccharide precursors using mainly thioglycosides as glycosyl donors. Stereospecificity in the formation of the α-linked monoester H-phosphonate was possible in type c through crystallization of the pure α-anomer of the precursor hemiacetal from an α/β-mixture, whereas in type f, the hemiacetal was isolated directly as exclusively the α-anomer. Subsequent phosphonylation using triimidazolylphosphine was performed without anomerization. Formation of the anomeric phosphate diester linkages was performed using pivaloyl chloride as coupling reagent followed by I(2)/H(2)O oxidation of the formed diester H-phosphonates. Original experiments afforded no diester product at all, but optimization of the oxidation conditions (lowering the temperature and dilution with pyridine prior to I(2) addition) gave the dimers in good yields (71% and 81%) and, subsequently, after removal of a temporary silyl protecting group in the dimers, the trimers in fair yields (36% and 37%), accompanied by hydrolysis of the dimer phosphate linkage. One-step deprotection through catalytic hydrogenolysis efficiently afforded the target dimer (30 and 36) and trimer structures (32 and 39). The synthetic scheme allows for further elongation to give higher oligomers

  Haemophilus influenzae, capsular polysaccharide, polysaccharides, chemical structure, oligomers, Post-translational modification

  NCBI PubMed ID: 11559168
  Publication DOI: 10.1021/jo001302m
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
  
   
  
  Haemophilus influenzae c
  CSDB ID 6952 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_120354,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7

• Article ID: 251
  Hansson J, Garegg PJ, Oscarson S "Syntheses of anomerically phosphodiester-linked oligomers of the repeating units of the Haemophilus influenzae types c and f capsular polysaccharides" - Journal of Organic Chemistry 66(19) (2001) 6234-6243
  

  Spacer-equipped dimers and trimers of the repeating units of the capsular polysaccharide of Haemophilus influenzae type c, -4)-3-O-Ac-β-d-GlcpNAc-(1→3)-α-d-Galp-(1-OPO3−, and type f, −3)-β-d-GalpNAc-(1→4)-3-O-Ac-α-d-GalpNAc-(1-OPO3-, have been synthesized for use in immunological studies. H-Phosphonate chemistry was used for the formation of the interglycosidic phosphate diester linkages. Two types of building blocks, a spacer glycoside disaccharide starting monomer (15 and 22) and an anomeric monoester α-H-phosphonate disaccharide elongating monomer (12 and 27), were built up for each serotype structure from properly protected monosaccharide precursors using mainly thioglycosides as glycosyl donors. Stereospecificity in the formation of the α-linked monoester H-phosphonate was possible in type c through crystallization of the pure α-anomer of the precursor hemiacetal from an α/β-mixture, whereas in type f, the hemiacetal was isolated directly as exclusively the α-anomer. Subsequent phosphonylation using triimidazolylphosphine was performed without anomerization. Formation of the anomeric phosphate diester linkages was performed using pivaloyl chloride as coupling reagent followed by I(2)/H(2)O oxidation of the formed diester H-phosphonates. Original experiments afforded no diester product at all, but optimization of the oxidation conditions (lowering the temperature and dilution with pyridine prior to I(2) addition) gave the dimers in good yields (71% and 81%) and, subsequently, after removal of a temporary silyl protecting group in the dimers, the trimers in fair yields (36% and 37%), accompanied by hydrolysis of the dimer phosphate linkage. One-step deprotection through catalytic hydrogenolysis efficiently afforded the target dimer (30 and 36) and trimer structures (32 and 39). The synthetic scheme allows for further elongation to give higher oligomers

  Haemophilus influenzae, capsular polysaccharide, polysaccharides, chemical structure, oligomers, Post-translational modification

  NCBI PubMed ID: 11559168
  Publication DOI: 10.1021/jo001302m
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
  
   
  
  Haemophilus influenzae c
  CSDB ID 6953 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_7

• Article ID: 264
  Hoog C, Laaksonen A, Widmalm G "Molecular dynamics simulations of the phosphodiester-linked repeating units of the Haemophilus influenzae types c and f capsular polysaccharides" - Journal of Physical Chemistry B 105(29) (2001) 7074-7079
  

  The three-dimensional structure of the repeating units of Haemophilus influenzae types c and f capsular polysaccharides (CPS) have been investigated by molecular dynamics simulations. The models consist of disaccharides joined by phosphodiester linkages, explicit water, and sodium as the counterion. Four 1 ns simulations were performed for each type, with either different starting conformations or different methods to handle long-range truncation effects, namely, Ewald summation or force shift truncation. For the average properties investigated, the choice of the method did not make any significant difference. Limited flexibility was observed close to the sugar residues, whereas at the phosphorus atom, the torsions showed major transitions. For comparison, 3./n,p was measured on CPS material. On the basis of these spin-spin couplings, only small changes are required in the models of the disaccharide repeating unit to agree with data on the CPS. In addition, hydrogen bonding and radial and spatial distribution functions were analyzed to obtain a picture of solvent ordering around the disaccharides.

  Haemophilus, Haemophilus influenzae, capsular polysaccharides, polysaccharides, type, molecular dynamics, simulation

  Publication DOI: 10.1021/jp0041555
  Journal NLM ID: 101157530
  Publisher: Washington, DC: American Chemical Society
  Correspondence: G. Widmalm
  Institutions: Department of Organic Chemistry and Division of Physical Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
  Methods: 1H NMR, 31P NMR
  
   
  
  Haemophilus influenzae c
  CSDB ID 7242 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_885822,SB_7

• Article ID: 628
  Bartodziejska B, Toukach FV, Vinogradov EV, Senchenkova SN, Shashkov AS, Ziolkowski A, Czaja J, Perry MB, Knirel YA, Rozalski A "Structural and serological studies of two related O-specific polysaccharides of Proteus vulgaris O21 and Proteus mirabilis O48 having oligosaccharide-phosphate repeating units" - European Journal of Biochemistry 267 (2000) 6888-6896
  

  The O-specific polysaccharide chains (O-antigens) of the lipopolysaccharides (LPSs) of Proteus mirabilis O48 and Proteus vulgaris O21 were found to have tetrasaccharide and pentasaccharide repeating units, respectively, interlinked by a glycosidic phosphate. Polysaccharides and an oligosaccharide were derived from the LPSs by various degradation procedures and studied by 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, H-detected 1H,13C and 1H,31P HMQC experiments. The following related structures of the repeating units of the O-antigens were established (top: Proteus mirabilis O48; bottom: Proteus vulgaris O21). The O-specific polysaccharide of P. vulgaris O21 has the same structure as that of Hafnia allvei 744 and PCM1194 [Petersson C., Jachymek, W., Klonowska, A., Lugowski, C., Niedziela, T. & Kenne, L. (1997) Eur. J. Biochem., 245, 668-675], except that the GlcN residue carries the N-acetyl rather than the N-[(R)-3-hydroxybutyryl] group. Serological investigations confirmed the close relatedness of the Proteus and Hafnia O-antigens studied.

  Lipopolysaccharide, NMR, O-antigen, O-specific polysaccharide, Proteus, Proteus mirabilis, Proteus vulgaris, 3-Acetamido-3, 6-dideoxy-d-glucose, Serological cross-reactivity

  NCBI PubMed ID: 11082201
  Publication DOI: 10.1046/j.1432-1033.2000.01793.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: rozala@biol.uni.lodz.pl
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Poland
  Methods: NMR-2D, EIA, ESI-MS, GLC, alkaline degradation, deamination, acid degradation, passive hemolysis test(PHT)
  
   
  
  Proteus mirabilis O48
  CSDB ID 88 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_885822,SB_7

• Article ID: 709
  Kaca W, Swierzko AS, Ziolkowski A, Amano K, Senchenkova SN, Knirel YA "Serological studies of an acid-labile O-polysaccharide of Proteus vulgaris OX19 lipopolysaccharide using human and rabbit antibodies" - Microbiology and Immunology 42(10) (1998) 669-675
  

  In a Weil-Felix test, sera from patients infected with Rickettsia sp. agglutinate Proteus OX types of bacteria and Proteus lipopolysaccharide (LPS) are responsible for the cross-reaction. Data on the character of LPS of one of the OX group strains, Proteus vulgaris OX19, are contradictory, and it remained unclear whether it has an O-polysaccharide (OPS) and is thus LPS of the smooth type (S) or not (rough-type LPS). Our studies showed that P. vulgaris OX19 (strain PZH-24) produces a smooth-type LPS that contains a long-chain OPS, but it undergoes depolymerization during mild acid hydrolysis conventionally used for LPS delipidation and loses the serological activity. An elucidation of the complete structure of OPS demonstrated the presence of a glycosyl phosphate linkage responsible for the acid-lability of the polysaccharide chain. In ELISA, both IgM type antibodies in a Weil-Felix test with human anti-Rickettsia typhi sera and rabbit anti-P. vulgaris OX19 antibodies reacted with OPS. Rabbit antibodies did not inhibit the cross-reaction with human antibodies and thus bind to different epitopes.

  Lipopolysaccharide, LPS, human, structural, characterization, O-antigen, antibodies, antibody, O-polysaccharide, O polysaccharide, Proteus, serological, immunochemical, Proteus vulgaris, comparison, reaction, cross-reactive, cross-reaction, 2-acetamido-2-deoxy-D-glucose, rabbit, Weil-Felix test

  NCBI PubMed ID: 9858461
  Journal NLM ID: 7703966
  Publisher: Japanese Society For Bacteriology
  Correspondence: wkaca@wirus.cmiwpan.lodz.pl
  Institutions: Centre of Microbiology and Virology, Lodz, Poland
  Methods: NMR, de-O-acetylation
  
   
  
  Proteus vulgaris OX19
  CSDB ID 826 (all data & tools)
• Article ID: 1190
  Senchenkova SN, Shashkov AS, Toukach FV, Ziolkowski A, Swierzko A, Amano K, Kaca W, Knirel YA, Kochetkov NK "Structure of the acid-labile galactosyl phosphate-containing O-antigen of Proteus vulgaris OX19 (serogroup O1) used in the Weil-Felix test" - Biochemistry (Moscow) 62(5) (1997) 461-468
  

  Lipopolysaccharide, LPS, structure, structural, polysaccharide, O-antigen, O antigen, phosphate, 2-acetamido-2, Proteus, serological, serology, serogroup, Glycosyl phosphate, Proteus vulgaris, Weil-Felix test, rickettsia, 6-dideoxy-L-glucose, diagnostic, Rickettsia japonica, test

  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: knirel@ioc.ac.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: NMR
  
   
  
  Proteus vulgaris OX19
  CSDB ID 4634 (all data & tools)
• 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: 7901356
  WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895
  Publisher: 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 ŁódźŸ, Banacha 12/16, 90-237 ŁódŸź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 ŁódźŸ, Poland
  
   
  
  Proteus vulgaris O1 (OX19)
  CSDB ID 2819 (all data & tools)
• 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: 17092493
  Publication DOI: 10.1016/j.carres.2006.10.006
  Journal NLM ID: 0043535
  Publisher: 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.
  
   
  
  Proteus vulgaris O1, Proteus vulgaris OX19
  CSDB ID 21774 (all data & tools)
• Article ID: 5760
  Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" - Molecular Immunology 120 (2020) 74-82
  

  To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.

  cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen

  NCBI PubMed ID: 32087569
  Publication DOI: 10.1016/j.molimm.2020.02.005
  Journal NLM ID: 7905289
  Publisher: Elsevier
  Correspondence: professorbovin@yandex.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
  Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
  
   
  
  Proteus vulgaris OX19
  CSDB ID 3973 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1394181,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_145001,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_885822,IEDB_983931,SB_192,SB_21,SB_7

• Article ID: 772
  Cisar JO, Sandberg AL, Reddy GP, Abeygunawardana C, Bush CA "Structural and antigenic types of cell wall polysaccharides from viridans group streptococci with receptors for oral actinomyces and streptococcal lectins" - Infection and Immunity 65(12) (1997) 5035-5041
  

  Lectin-mediated interactions between oral viridans group streptococci and actinomyces may play an important role in microbial colonization of the tooth surface. The presence of two host-like motifs, either GalNAc β1→3 Gal (Gn) or Gal β1→3 GalNAc (G), in the cell wall polysaccharides of five streptococcal strains accounts for the lactose-sensitive coaggregations of these bacteria with Actinomyces naeslundii. Three streptococcal strains which have Gn-containing polysaccharides also participate in GalNAc-sensitive coaggregations with strains of Streptococcus gordonii and S. sanguis. Each Gn- or G-containing polysaccharide is composed of a distinct phosphodiester-linked hexa- or heptasaccharide repeating unit. The occurrence of these polysaccharides on 19 additional viridans group streptococcal strains that participate in lactose-sensitive coaggregations with actinomyces was examined. Negatively charged polysaccharides that reacted with Bauhinia purpurea agglutinin, a Gal and GalNAc binding plant lectin, were isolated from 17 strains by anion exchange column chromatography of mutanolysin-cell wall digests. Results from nuclear magnetic resonance and immunodiffusion identified each of 16 polysaccharides as a known Gn- or G-containing structural type and one polysaccharide as a new but closely related Gn-containing type. Unlike the reactions of lectins, the cross-reactions of most rabbit antisera with these polysaccharides were correlated with structural features other than the host-like motifs. Gn-containing polysaccharides occurred primarily on the strains of S. sanguis and S. oralis while G-containing polysaccharides were more common among the strains of S. gordonii and S. mitis examined. The findings strongly support the hypothesis that lectin-mediated recognition of these streptococci by other oral bacteria depends on a family of antigenically diverse Gn- and G-containing cell wall polysaccharides, the occurrence of which may differ between streptococcal species.

  Streptococcus, cell wall polysaccharides, lectins, Actinomyces, receptors, streptococcal

  NCBI PubMed ID: 9393793
  Publication DOI: 10.1128/IAI.65.12.5035-5041.1997
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: jcisar@yoda.nidr.nih.gov
  Institutions: Oral Infection and Immunity Branch, National Institute of Dental Research, National Institutes of Health, bethasda, Maryland 20892, Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Mareland 21228
  Methods: 1H NMR
  
   
  
  Streptococcus oralis 34, Streptococcus oralis SK111, Streptococcus sanguis SK72, Streptococcus sanguis SK75, Streptococcus sanguis SK77, Streptococcus sanguis SK163, Streptococcus sanguis SK45, Streptococcus sanguis SK112
  CSDB ID 1233 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1394181,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_145001,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_885822,IEDB_983931,SB_192,SB_21,SB_7

• Article ID: 772
  Cisar JO, Sandberg AL, Reddy GP, Abeygunawardana C, Bush CA "Structural and antigenic types of cell wall polysaccharides from viridans group streptococci with receptors for oral actinomyces and streptococcal lectins" - Infection and Immunity 65(12) (1997) 5035-5041
  

  Lectin-mediated interactions between oral viridans group streptococci and actinomyces may play an important role in microbial colonization of the tooth surface. The presence of two host-like motifs, either GalNAc β1→3 Gal (Gn) or Gal β1→3 GalNAc (G), in the cell wall polysaccharides of five streptococcal strains accounts for the lactose-sensitive coaggregations of these bacteria with Actinomyces naeslundii. Three streptococcal strains which have Gn-containing polysaccharides also participate in GalNAc-sensitive coaggregations with strains of Streptococcus gordonii and S. sanguis. Each Gn- or G-containing polysaccharide is composed of a distinct phosphodiester-linked hexa- or heptasaccharide repeating unit. The occurrence of these polysaccharides on 19 additional viridans group streptococcal strains that participate in lactose-sensitive coaggregations with actinomyces was examined. Negatively charged polysaccharides that reacted with Bauhinia purpurea agglutinin, a Gal and GalNAc binding plant lectin, were isolated from 17 strains by anion exchange column chromatography of mutanolysin-cell wall digests. Results from nuclear magnetic resonance and immunodiffusion identified each of 16 polysaccharides as a known Gn- or G-containing structural type and one polysaccharide as a new but closely related Gn-containing type. Unlike the reactions of lectins, the cross-reactions of most rabbit antisera with these polysaccharides were correlated with structural features other than the host-like motifs. Gn-containing polysaccharides occurred primarily on the strains of S. sanguis and S. oralis while G-containing polysaccharides were more common among the strains of S. gordonii and S. mitis examined. The findings strongly support the hypothesis that lectin-mediated recognition of these streptococci by other oral bacteria depends on a family of antigenically diverse Gn- and G-containing cell wall polysaccharides, the occurrence of which may differ between streptococcal species.

  Streptococcus, cell wall polysaccharides, lectins, Actinomyces, receptors, streptococcal

  NCBI PubMed ID: 9393793
  Publication DOI: 10.1128/IAI.65.12.5035-5041.1997
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: jcisar@yoda.nidr.nih.gov
  Institutions: Oral Infection and Immunity Branch, National Institute of Dental Research, National Institutes of Health, bethasda, Maryland 20892, Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Mareland 21228
  Methods: 1H NMR
  
   
  
  Streptococcus gordonii 38, Streptococcus oralis B2, Streptococcus oralis SK92, Streptococcus oralis M9811
  CSDB ID 1322 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,SB_7

• Article ID: 1213
  Shashkov AS, Senchenkova SN, Nazarenko EL, Zubkov VA, Gorshkova NM, Knirel YA, Gorshkova RP "Structure of a phosphorylated polysaccharide from Shewanella putrefaciens strain S29" - Carbohydrate Research 303 (1997) 333-338
  

  oligosaccharide, structure, strain, polysaccharide, capsular polysaccharide, phosphate, 2-acetamido-2, phosphorylated, 6-dideoxy-d-glucose, Shewanella, galactose, 4-Acetamido-4, 6-dideoxy-L-glucose, absolute configuration, Shewanella putrifaciens

  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: partial acid hydrolysis, NMR
  
   
  
  Shewanella putrefaciens S29
  CSDB ID 4666 (all data & tools)
• 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: 17092493
  Publication DOI: 10.1016/j.carres.2006.10.006
  Journal NLM ID: 0043535
  Publisher: 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.
  
   
  
  Shewanella putrefaciens S29
  CSDB ID 21788 (all data & tools)
• Article ID: 4434
  Nazarenko EL, Komandrova NA, Gorshkova RP, Tomshich SV, Zubkov VA, Kilcoyne M, Savage AV "Structures of polysaccharides and oligosaccharides of some Gram-negative marine Proteobacteria" - Carbohydrate Research 338(23) (2003) 2449-2457
  

  The chemical structures of polysaccharides and LPS core oligosaccharides, isolated from various Gram-negative marine bacteria from the genera Pseudoalteromonas and Shewanella belonging to the Alteromonadaceae family and gamma-subclass of Proteobacteria, are reviewed. The polysaccharides are distinguished by the acidic character (e.g., due to the presence of hexuronic and aldulosonic acids and their derivatives) and the occurrence of unusual sugars, including N-acyl derivatives of 6-deoxyamino sugars, such as N-acetyl-D-quinovosamine, N-acetyl-L-fucosamine and N-acetyl-6-deoxy-L-talosamine, and higher sugars like 2,6-dideoxy-2-acetamido-4-C-(3'-carboxamide-2',2'-dihydroxypropyl)-D-galac topyranose (shewanellose). Many constituent sugars have various uncommon non-sugar substituents, such as alanine, formic, lactic and hydroxybutyric acids, sulfate, phosphate, and 2-aminopropane-1,3-diol.

  Lipopolysaccharide, oligosaccharide structure, O-antigen, polysaccharide structure, Shewanella, Pseudoalteromonas, Proteobacteria

  NCBI PubMed ID: 14670708
  Publication DOI: 10.1016/j.carres.2003.06.004
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: A.V. Savage
  Institutions: Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation
  
   
  
  Shewanella putrefaciens S29
  CSDB ID 28839 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_145001,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_885822,SB_7

• Article ID: 1332
  Ziolkowski A, Shashkov AS, Swierzko A, Senchenkova SN, Toukach FV, Cedzynski M, Amano K, Kaca W, Knirel YA "Structures of the O-antigens of Proteus bacilli belonging to OX group (serogroups O1-O3) used in Weil-Felix test" - FEBS Letters 411 (1997) 221-224
  

  Structures of the O-specific polysaccharide chains of lipopolysaccharides from Proteus group OX strains (serogroups O1-O3) used as antigens in Weil-Felix test for diagnosis of rickettsiosis, were established. From them, the acid-labile polysaccharide of Proteus vulgaris OX19(O1) is built up of the following branched pentasaccharide repeating units connected via a phosphate group: [structure in text] where QuiNAc stands for 2-acetamido-2,6-dideoxyglucose (N-acetylquinovosamine). The basis of serospecificity of the Proteus group OX antigens and their cross-reactivity with human anti-rickettsial antibodies is discussed

  Lipopolysaccharide, O-antigen, Proteus, bacterial polysaccharide structure, Serological cross-reactivity, Weil-Felix test, rickettsia, rickettsiosis

  NCBI PubMed ID: 9271209
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: knirel@ioc.ac.ru
  Institutions: Center of Microbiology and Virology, Polish Academy of Sciences, Lodz, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Central Research Laboratory, Akita University, School of Medicine, Akita, Japan
  Methods: NMR-2D, methylation, NMR, de-O-acetylation
  
   
  
  Proteus vulgaris OX19
  CSDB ID 5985 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: coaggregation receptor polysaccharide (RPS)
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_145001,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885822,IEDB_885823,IEDB_983931,SB_192,SB_21,SB_7

• Article ID: 1401
  Cisar JO, Sandberg AL, Abeygunawardana C, Reddy GP, Bush CA "Lectin recognition of host-like saccharide motifs in streptococcal cell wall polysaccharides" - Glycobiology 5 (1995) 655-662
  

  Viridans streptococci that participate in the microbial colonization of teeth have cell wall polysaccharides composed of linear phosphodiester-linked hexa- or heptasaccharide repeating units, each containing a host-like disaccharide motif, either Gal β1→3 GalNAc or GalNAc β1→3 Gal. Whereas strains with GalNAc β1→ Gal-containing polysaccharides co-aggregated with streptococci that possess GalNAc-sensitive lectins, strains with either host-like motif co-aggregated with Actinomyces spp. The latter interactions reflected the specificity of Actinomyces spp. lectins for common features of Gal β1→3 GalNAc and GalNAc β1→3 Gal. Thus, α-linked glycosides of both disaccharides were much more potent inhibitors of co-aggregation than Gal or GalNAc. Six non-bacterial lectins also reacted with the streptococcal polysaccharides. In general, precipitation of each lectin with each polysaccharide involved binding of Gal or GalNAc within the host-like motifs, but not saccharides outside these regions. The lectins of Ricinus communis, Abrus precatorius, Codium fragile and Agaricus bisporus were most reactive with the Gal β1→3 GalNAc-containing polysaccharides, the Wisteria floribunda lectin with the GalNAc β1→3 Gal-containing polysaccharides and the Bauhinia purpurea lectin with polysaccharides containing either disaccharide. Thus, lectin recognition of the streptococcal cell wall polysaccharides involved either the common or specific sides of the Gal β1→3 GalNAc and GalNAc β1→3 Gal motifs present within these molecules.

  lectins, bacterial adhesins, cellular recognition, microbial colonization, streptococcal polysaccharides

  NCBI PubMed ID: 8608267
  Publication DOI: 10.1093/glycob/5.7.655
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Laboratory of Microbial Ecology, National Institute of Dental Research, National Institutes of Health, Bethesda, MD, USA
  
   
  
  Streptococcus oralis 34
  CSDB ID 6645 (all data & tools)
• Article ID: 1757
  Abeygunawardana C, Bush CA, Cisar JO "Complete structure of the polysaccharide from Streptococcus sanguis J22" - Biochemistry 29 (1990) 234-248
  

  The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22 which is composed of a heptasaccharide subunit linked by phosphodiester bonds. The repeating subunit, which contains α-GalNAc, α-rhamnose, β-rhamnose, β-glucose, and β-galactose all in the pyranoside form and β-galactofuranose, is compared with the previously published structure of the polysaccharide from strain 34. The structure has been determined almost exclusively by high-resolution nuclear magnetic resonance methods. The 1H and 13C NMR spectra of the polysaccharides from both strains 34 and J22 have been completely assigned. The stereochemistry of pyranosides was assigned from JH-H values determined from phase-sensitive COSY spectra, and acetamido sugars were assigned by correlation of the resonances of the amide 1H with the sugar ring protons. The 13C spectra were assigned by 1H-detected multiple-quantum correlation (HMQC) spectra, and the assignments were confirmed by 1H-detected multiple-bond correlation (HMBC) spectra. The positions of the glycosidic linkages were assigned by detection of three-bond 1H-13C correlation across the glycosidic linkage in the HMBC spectra. The positions of the phosphodiester linkages were determined by splittings observed in the 13C resonances due to 31P coupling and also by 1H-detected 31P correlation spectroscopy.

  NCBI PubMed ID: 2157479
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Department of Chemistry, Illinois Institute of Technology, Chicago 60616
  Methods: 13C NMR, 1H NMR
  
   
  
  Streptococcus mitis J22
  CSDB ID 107544 (all data & tools)
• Article ID: 2142
  Abeygunawardana C, Bush CA, Tjoa SS, Fennessey PV, McNeil MR "The complete structure of the capsular polysaccharide from Streptococcus sanguis 34" - Carbohydrate Research 191 (1989) 279-293
  

  A complete structure for the capsular polysaccharide of Streptococcus sanguis 34, which is responsible for coaggregation of this bacterium with Actinomyces viscosus T14V, an important step in the formation of dental plaque, is proposed, based partly on the 1H-n.m.r. spectrum, which was assigned by 2-dimensional COSY, homonuclear Hartmann-Hahn spectroscopy, and nuclear Overhauser effects. A phosphoric diester linkage was identified from the 31P-n.m.r. spectrum, and the linkage was determined from long range 1H-31P correlation spectroscopy. The proposed structure is supported both by methylation analysis before and after dephosphorylation and by g.l.c.-m.s. of the phosphorylated monosaccharides as their trimethylsilyl derivatives, isolated by partial hydrolysis of the polysaccharide. The structure is composed of repeating linear hexasaccharide units joined by a phosphoric diester linkage, i.e., [→PO4(-)→6)-α-D-GalpNAc-(1→3)-β-L-Rhap-(1→4)-β-D-Glcp- (1→6)-β-D-Galf-(1→6)-β-D-GalpNAc-(1→3)-α-D-Galp-(1→]n.

  NCBI PubMed ID: 2582463
  Publication DOI: 10.1016/0008-6215(89)85071-2
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Chemistry, Illinois Institute of Technology, Chicago 60616
  Methods: 1H NMR, NMR-2D, GLC-MS, 31P NMR, GLC, HF treatment
  
   
  
  Streptococcus sanguinis 34
  CSDB ID 115742 (all data & tools)
• Article ID: 4140
  Yang J, Cisar JO, Bush CA "Structure of type 3Gn coaggregation receptor polysaccharide from Streptococcus cristatus LS4" - Carbohydrate Research 346(11) (2011) 1342-1346
  

  The presence of a novel coaggregation receptor polysaccharide (RPS) on the dental plaque isolate Streptococcus cristatus LS4 was suggested by this strain's antigenic and coaggregation properties. Examination of RPS isolated from strain LS4 by a combination of 2-dimensional and pseudo 3-dimensional single quantum heteronuclear NMR methods that included detection of (13)C chemical shifts at high resolution revealed the following repeat unit structure: →6)-β-D-Galf-(1→6)-β-D-GalpNAc-(1→3)-α-D-Galp-(1→P→6)-α-D-Galp-(1→3)-β-L-Rhap-(1→4)-β-D-Glcp-(1→. The identification of this polysaccharide as RPS3Gn, a new structural type, was established by the α-D-Galp-containing epitope of RPS serotype 3 and Gn recognition motif (i.e., β-D-GalpNAc (1→3)-α-D-Galp) for coaggregation with other bacteria

  structure, polysaccharides, NMR spectroscopy, Oral bacteria

  NCBI PubMed ID: 21601178
  Publication DOI: 10.1016/j.carres.2011.04.035
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: C.A. Bush
  Institutions: Oral Infection and Immunity Branch, National Institute of Dental and Craniofacial Research, National Institutes of Health, Bethesda, MD 20892, United States
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, GC-MS, sugar analysis, serological methods, immunoblotting, enzymatic digestion, NMR-3D
  
   
  
  Streptococcus oralis 34
  CSDB ID 27021 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Contained glycoepitopes: IEDB_130648,IEDB_133754,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_145001,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885822,IEDB_885823,IEDB_983931,SB_192,SB_21,SB_7

• Article ID: 1401
  Cisar JO, Sandberg AL, Abeygunawardana C, Reddy GP, Bush CA "Lectin recognition of host-like saccharide motifs in streptococcal cell wall polysaccharides" - Glycobiology 5 (1995) 655-662
  

  Viridans streptococci that participate in the microbial colonization of teeth have cell wall polysaccharides composed of linear phosphodiester-linked hexa- or heptasaccharide repeating units, each containing a host-like disaccharide motif, either Gal β1→3 GalNAc or GalNAc β1→3 Gal. Whereas strains with GalNAc β1→ Gal-containing polysaccharides co-aggregated with streptococci that possess GalNAc-sensitive lectins, strains with either host-like motif co-aggregated with Actinomyces spp. The latter interactions reflected the specificity of Actinomyces spp. lectins for common features of Gal β1→3 GalNAc and GalNAc β1→3 Gal. Thus, α-linked glycosides of both disaccharides were much more potent inhibitors of co-aggregation than Gal or GalNAc. Six non-bacterial lectins also reacted with the streptococcal polysaccharides. In general, precipitation of each lectin with each polysaccharide involved binding of Gal or GalNAc within the host-like motifs, but not saccharides outside these regions. The lectins of Ricinus communis, Abrus precatorius, Codium fragile and Agaricus bisporus were most reactive with the Gal β1→3 GalNAc-containing polysaccharides, the Wisteria floribunda lectin with the GalNAc β1→3 Gal-containing polysaccharides and the Bauhinia purpurea lectin with polysaccharides containing either disaccharide. Thus, lectin recognition of the streptococcal cell wall polysaccharides involved either the common or specific sides of the Gal β1→3 GalNAc and GalNAc β1→3 Gal motifs present within these molecules.

  lectins, bacterial adhesins, cellular recognition, microbial colonization, streptococcal polysaccharides

  NCBI PubMed ID: 8608267
  Publication DOI: 10.1093/glycob/5.7.655
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Laboratory of Microbial Ecology, National Institute of Dental Research, National Institutes of Health, Bethesda, MD, USA
  
   
  
  Streptococcus gordonii 38
  CSDB ID 6646 (all data & tools)
• Article ID: 1663
  Yoshida Y, Ganguly S, Bush CA, Cisar JO "Carbohydrate engineering of the recognition motifs in streptococcal co-aggregation receptor polysaccharides" - Molecular Microbiology 58(1) (2005) 244-256
  

  The cell wall polysaccharides of certain oral streptococci function as receptors for the lectin-like surface adhesins on other members of the oral biofilm community. Recognition of these receptor polysaccharides (RPS) depends on the presence of a host-like motif, either GalNAcβ1-3Gal (Gn) or Galβ1-3GalNAc (G), within the oligosaccharide repeating units of different RPS structural types. Type 2Gn RPS of Streptococcus gordonii 38 and type 2G RPS of Streptococcus oralis J22 are composed of heptasaccharide repeats that are identical except for their host-like motifs. In the current investigation, the genes for the glycosyltransferases that synthesize these motifs were identified by high-resolution nuclear magnetic resonance (NMR) analysis of genetically altered polysaccharides. RPS production was switched from type 2Gn to 2G by replacing wefC and wefD in the type 2Gn gene cluster of S. gordonii 38 with wefF and wefG from the type 2G cluster of S. oralis J22. Disruption of either wefC or wefF abolished cell surface RPS production. In contrast, disruption of wefD in the type 2Gn cluster or wefG in the type 2G cluster eliminated β-GalNAc from the Gn motif or β-Gal from the G motif, resulting in mutant polysaccharides with hexa- rather than heptasaccharide subunits. The mutant polysaccharides reacted like wild-type RPS with rabbit antibodies against type 2Gn or 2G RPS but were inactive as co-aggregation receptors. Additional mutant polysaccharides with GalNAcβ1-3GalNAc or Galβ1-3Gal recognition motifs were engineered by replacing wefC in the type 2Gn cluster with wefF or wefF in the type 2G cluster with wefC respectively. The reactions of these genetically modified polysaccharides as antigens and receptors provide further insight into the structural basis of RPS function.

  polysaccharide, polysaccharides, carbohydrate, recognition, motif, engineering, streptococcal, receptor

  NCBI PubMed ID: 16164562
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Correspondence: john.cisar@nih.gov
  Institutions: Oral Infection and Immunity Branch, National Institute of Dental and Craniofacial Research, National Institutes of Health, Bethesda, MD, USA, Department of Chemistry and Biochemistry, University of Maryland Baltimore County, Baltimore, MD 21250, USA
  Methods: NMR
  
   
  
  Streptococcus gordonii 38
  CSDB ID 10651 (all data & tools)
• 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: 17092493
  Publication DOI: 10.1016/j.carres.2006.10.006
  Journal NLM ID: 0043535
  Publisher: 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.
  
   
  
  Streptococcus gordonii 38, Streptococcus oralis 38
  CSDB ID 21816 (all data & tools)