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1. Compound ID: 189
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-Glcp2Ac-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144826,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
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2. Compound ID: 416
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-4)-a-D-GlcpA2Ac3Ac-(1-3)-a-D-Galp-(1-3)-b-D-ManpNAc4Ac6Ac-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp2Ac3Ac-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_885813,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 146
van Selm S, Kolkman MA, van der Zeijst BA, Zwaagstra KA, Gaastra W, van Putten JP "Organization and characterization of the capsule biosynthesis locus of Streptococcus pneumoniae serotype 9V" -
Microbiology 148(6) (2002) 1747-1755
The capsular polysaccharide (CPS) synthesis locus of Streptococcus pneumoniae serotype 9V was amplified by long-range PCR and sequenced. The locus was 17368 bp in size and contained 15 ORFs. The genetic organization of the cluster shared many features with other S. pneumoniae capsule loci, including the presence of four putative regulatory genes at the 5' end. Comparative sequence analyses allowed putative functions to be assigned to each of the gene products. The ORFs appeared to encode, besides the four regulatory genes, five glycosyltransferases, two O-acetyltransferases, an N-acetylglucosamine 2-epimerase, a glucose 6-dehydrogenase, an oligosaccharide transporter protein and a polysaccharide repeating unit polymerase. These functions covered the steps proposed in the CPS biosynthesis of serotype 9V. TLC of carbohydrate intermediates formed after incubation of bacterial membrane preparations with 14C-labelled precursors demonstrated that the fifth ORF (cps9vE) encoded a UDP-glucosyl-1-phosphate transferase. This function was confirmed with the help of a cps9vE mutant that carried a deletion of a guanine residue located adjacent to a stretch of adenines. The identification and characterization of the serotype 9V locus is a major step in unravelling the 9V capsule biosynthesis pathway and broadens the insight into the genetic diversity of the S. pneumoniae capsule loci
capsular polysaccharide biosynthesis, glucosyltransferase
NCBI PubMed ID: 12055294Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: j.vanputten@vet.uu.nl
Institutions: Bacteriology Division, Department of Infectious Diseases and Immunology, Utrecht University, PO Box 80.165, 3508 TD Utrecht, The Netherlands, Genencor International B. V., 2300 AE Leiden, The Netherlands, National Institute of Public Health and the Environment, 3720 BA Bilthoven, The Netherlands
- Article ID: 293
Kolberg J, Jones C "Monoclonal antibodies with specificities for Streptococcus pneumoniae group 9 capsular polysaccharides" -
FEMS Immunology and Medical Microbiology 20(4) (1998) 249-255
Streptococcus pneumoniae group 9 includes four capsular polysaccharide types: 9A, 9L, 9N and 9V. We have generated four mouse monoclonal antibodies against group 9 polysaccharide using heat-treated S. pneumoniae strains of different capsular polysaccharides types as immunogens. The specificities of the monoclonal antibodies were determined by ELISA using capsular polysaccharide directly coated to the wells as antigens and by dot blotting with heat-treated bacteria. Two groups of monoclonal antibodies were found. The first group included two monoclonal antibodies which were found to be capsular type specific. The second group was monoclonal antibodies that bound to epitopes shared by two or three pneumococcal group 9 types. The monoclonal antibody 204,A-4 (IgM) was found to be specific for S. pneumoniae type 9N. The binding of the type 9V specific monoclonal antibody 206,F-5 (IgG1) was found to be dependent upon O-acetyl groups. Monoclonal antibody 205,F-3 (IgM) reacted also with type 9V, but was found to cross-react with types 9A and 9L. The binding of this monoclonal antibody to polysaccharide 9V was not dependent upon O-acetyl moieties. The fourth monoclonal antibody (214,G-5, isotype IgM) did not show any correlation between reactivity with isolated polysaccharides and dot blotting with relevant bacteria. The monoclonal antibody reacted with polysaccharides 9A and 9L in ELISA, but not with the homologous bacteria.
Streptococcus pneumoniae, capsular polysaccharides, monoclonal antibodies, group 9 polysaccharide
NCBI PubMed ID: 9626929Journal NLM ID: 9315554Publisher: Elsevier
Institutions: National Institute of Public Health, Department of Vaccinology, P.O. Box 4404 Torshov, N-0403 Oslo, Norway, National Institute for Biological Standards and Control, South Mimms, Herts. EN6 3QG, UK.
- Article ID: 4283
Calix JJ, Saad JS, Brady AM, Nahm MH "Structural characterization of Streptococcus pneumoniae serotype 9A capsule polysaccharide reveals role of glycosyl 6-O-acetyltransferase wcjE in serotype 9V capsule biosynthesis and immunogenicity" -
Journal of Biological Chemistry 287(17) (2012) 13996-14003
The putative capsule O-acetyltransferase gene wcjE is highly conserved across various Streptococcus pneumoniae serotypes, but the role of the gene in capsule biosynthesis and bacterial fitness remains largely unclear. Isolates expressing pneumococcal serotype 9A arise from precursors expressing wcjE-associated serotype 9V through loss-of-function mutation to wcjE. To define the biosynthetic role of 9V wcjE, we characterized the structure and serological properties of serotype 9V and 9A capsule polysaccharide (PS). NMR data revealed that both 9V and 9A PS are composed of an identical pentasaccharide repeat unit, as reported previously. However, in sharp contrast to previous studies on 9A PS being devoid of any O-acetylation, we identified O-acetylation of α-glucuronic acid and α-glucose in 9A PS. In addition, 9V PS also contained -CH(2) O-acetylation of β-N-acetylmannosamine, a modification that disappeared following in vitro recombinatorial deletion of wcjE. We also show that serotyping sera and monoclonal antibodies specific for 9V and 9A bound capsule PS in an O-acetate-dependent manner. Furthermore, IgG and to a lesser extent IgM from human donors immunized with serotype 9V PS displayed stronger binding to 9V compared with 9A PS. We conclude that serotype 9V wcjE mediates 6-O-acetylation of β-N-acetylmannosamine. This PS modification can be selectively targeted by antibodies in immunized individuals, identifying a potential selective advantage for wcjE inactivation and serotype 9A emergence.
structure, capsule polysaccharide, capsule biosynthesis, O-acetyltransferase, Streptococcus pneumoniae 9A, wcjE
NCBI PubMed ID: 22367197Publication DOI: 10.1074/jbc.M112.346924Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: nahm@uab.edu
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama 35294, USA
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, ELISA, de-O-acetylation, NMR-1D, serological methods
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3. Compound ID: 894
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/Variants 0/-+
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-4)-a-L-Rhap-(1-3)-b-D-Glcp2Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1-
/Variants 0/ is:
a-L-Rhap-(1-3)-
OR (exclusively)
a-L-Manp-(1-3)- |
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Structure type: polymer chemical repeating unit
Trivial name: welan
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_135849,IEDB_136105,IEDB_1394182,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 252
Hashimoto W, Murata K "a-L-rhamnosidase of Sphingomonas sp. R1 producing an unusual exopolysaccharide of sphingan" -
Bioscience, Biotechnology, and Biochemistry 62(6) (1998) 1068-1074
A soil bacterium with α-L-rhamnosidase was isolated from a cumulative mixed culture containing a polysaccharide of gellan as a carbon source and identified to be Sphingomonas paucimobilis, known as a potent producer of gellan. The isolate (designated Sphingomonas sp. R1) produced an unusual exopolysaccharide of sphingan (denoted HWR1) distinct from gellan. The rhamnose in gellan was replaced with mannose in HWR1. The bacterium had a peculiar cell surface covered with many complicated plaits. α-L-Rhamnosidase purified from Sphingomonas sp. R1 grown in the presence of naringin was a monomer with a molecular mass of 110 kDa and most active at pH 8.0 and 50 degrees C. The enzyme required divalent metal ions for the activity and released L-rhamnose from various rhamnosyl glycosides.
polysaccharide, Sphingomonas, exopolysaccharide, sphingan, a-L-rhamnosidase
NCBI PubMed ID: 9692187Publication DOI: 10.1271/bbb.62.1068Journal NLM ID: 9205717Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Correspondence: hasimoto@food2.food.kyoto-u.ac.jp
Institutions: Research Institute for Food Science, Kyoto University, Uji 611-0011, Japan
Methods: SDS-PAGE, TLC, acid hydrolysis, HPLC, electron microscopy, enzyme assay
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 6146
Sun X, Zhang J "Bacterial exopolysaccharides: Chemical structures, gene clusters and genetic engineering" -
International Journal of Biological Macromolecules 173 (2021) 481-490
In recent decades, the composition, structure, biosynthesis, and function of bacterial extracellular polysaccharides (EPS) have been extensively studied. EPS are synthesized through different biosynthetic pathways. The genes responsible for EPS synthesis are usually clustered on the genome or large plasmids of bacteria. Generally, different EPS synthesis gene clusters direct the synthesis of EPS with different chemical structures and biological activities. A better understanding of the gene functions involved in EPS biosynthesis is critical for the production of EPS with special biological activities. Genetic engineering methods are usually used to study EPS synthesis related genes. This review organizes the available information on EPS, including their structures, synthesis of related genes, and highlights the research progress of modifying EPS gene clusters through gene-editing methods.
genetic engineering, gene clusters, bacterial extracellular polysaccharides
Publication DOI: 10.1016/j.ijbiomac.2021.01.139Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: jfzhang@mail.njust.edu.cn
Institutions: Center for Molecular Metabolism, Nanjing University of Science & Technology, Nanjing, China
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4. Compound ID: 1045
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D-Gro-(1--P--4)--+
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-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-Glcp2Ac3Ac-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_61,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 300
Lee CH, Frasch CE "Quantification of bacterial polysaccharides by the purpald assay: Measurement of periodate-generated formaldehyde from glycol in the repeating unit" -
Analytical Biochemistry 296(1) (2001) 73-82
We have adapted the purpald assay for measurement of bacterial polysaccharides (PS) containing substituted and/or unsubstituted glycol (SG or UG) in residues such as glycerol, ribitol, arabinitol, furanosyl galactose, and sialyl. For the purpald assay of UG-containing PS, 50 microL of PS samples was consecutively reacted with 50 microL of 16 mM NaIO4 for 20 min, 50 microL of 136 mM purpald reagent in 2 N NaOH for 20 min, and 50 microL of 64 mM NaIO4 for 20 min in a 96-well tissue culture plate followed by a measurement of absorbance at 550 nm with a plate reader. For SG-containing PS, conversion of SG to UG with 25 micro;L of 0.3 N NaOH, 1 h at room temperature for de-O-acetylation followed by 25 microL of 0.6 M H2SO4, 1 h at 80 degrees C for acid hydrolysis of PS precedes the periodate treatment in the purpald assay. The concentration of the samples can be calculated from the sample absorbance and the reference standard curve constructed from the reference concentrations of the same PS (well-characterized) and their corresponding absorbance values assayed in the same plate. The purpald assay provides a tool in addition to the existing ones for the measurement of glycol-containing PS. Among the usefulness of this method are the determinations of the glycerol content in the phospho-glycerol-containing PS and the SG and UG contents and structural integrity in PS and conjugate vaccines.
repeating unit, bacterial polysaccharides, quantification
NCBI PubMed ID: 11520034Publication DOI: 10.1006/abio.2001.5230Journal NLM ID: 0370535Publisher: Academic Press
Institutions: Laboratory of Bacterial Polysaccharides, Division of Bacterial, Parasitic and Allergenic Products, OVRR, CBER, FDA, 8800 Rockville Pike, Bethesda, MD, USA
Methods: purpald assay measurement
- Article ID: 506
Pujar NS, Huang NF, Daniels CL, Dieter L, Gayton MG, Lee AL "Base hydrolysis of phosphodiester bonds in pneumococcal polysaccharides" -
Biopolymers 75(1) (2004) 71-84
A comprehensive study of the base hydrolysis of all phosphodiester bond-containing capsular polysaccharides of the 23-valent pneumococcal vaccine is described here. Capsular polysaccharides from serotypes 6B, 10A, 17F, 19A, 19F, and 20 contain a phosphodiester bond that connects the repeating units in these polysaccharides (also referred to as backbone phosphodiester bonds), and polysaccharides from serotypes 11A, 15B, 18C, and 23F contain a phosphodiester bond that links a side chain to their repeating units. Molecular weight measurements of the polysaccharides, using high performance size exclusion chromatography with tandem multiangle laser light scattering and refractive index detection, was used to evaluate the kinetics of hydrolysis. The measurement of molecular weight provides a high degree of sensitivity in the case of small extents of reaction, thus allowing reliable measurements of the kinetics over short times. Pseudo-first-order rate constants for these polysaccharides were estimated using a simple model that accounts for the polydispersity of the starting sample. It was found that the relative order of backbone phosphodiester bond instability due to base hydrolysis was 19A > 10A > 19F > 6B > 17F, 20. Degradation of side-chain phosphodiester bonds was not observed, although the high degree of sensitivity in measurements is lost in this case, due to the low contribution of the side chains to the total polysaccharide molecular weight. In comparison with literature data on pneumococcal polysaccharide 6A, 19A was found to be the more labile, and hence appears to be the most labile pneumococcal polysaccharide studied to date. The rate of hydrolysis increased at higher pH and in the presence of divalent cation, but the extent was lower than expected based on similar data on RNA. Finally, the differences in the phosphodiester bond stabilities were analyzed by considering stereochemical factors in these polysaccharides. These results also provide a framework for evaluation of molecular integrity of phosphodiester-bond-containing polysaccharides in different solution conditions. Copyright 2004 Wiley Periodicals, Inc. Biopolymers, 2004
base hydrolysis, phosphodiester bond, pneumococcal polysaccharide
NCBI PubMed ID: 15307199Journal NLM ID: 0372525Publisher: Wiley Interscience
Correspondence: hari_pujar@merck.com
Institutions: Merck Research Laboratories, Merck & Co., West Point, PA 19486
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5. Compound ID: 1058
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a-Abep2Ac-(1-3)-+ a-D-Glcp2Ac-(1-4)-+
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-4)-b-L-Rhap2Ac-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_136,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_44,SB_61,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 309
Liu D, Lindqvist L, Reeves PR "Transferases of O-antigen biosynthesis in Salmonella enterica: Dideoxyhexosyltransferases of groups B and C2 and acetyltransferase of group C2" -
Journal of Bacteriology 177(14) (1995) 4084-4088
The O antigen is a polymer of oligosaccharide units. O antigens differ in their sugar composition and glycosidic linkages, and genes responsible for O-antigen-specific biosynthesis are grouped in the rfb gene cluster. In this study, we identified two abequosyltransferase genes and an acetyltransferase gene in Salmonella enterica groups B and C2 by in vitro assay and identified paratosyl-, tyvelosyl-, and abequosyltransferase genes from S. enterica groups A and D and Yersinia pseudotuberculosis serovar IIA, respectively, by comparison.
biosynthesis, O-antigen, transferase, Salmonella, Salmonella enterica, 3, 6-dideoxyhexose, acetyltransferase
NCBI PubMed ID: 7541787Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.su.oz.au
Institutions: Department of Microbiology, University of Sydney, New South Wales 2006, Australia, and Department of Clinical Bacteriology, Huddinge Hospital, Karolinska Institute, S-141 86 Huddinge, Sweden.
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6. Compound ID: 1130
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a-Abe-(1-3)-+ a-D-Glcp2Ac-(1-3)-+
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-4)-b-L-Rhap2Ac-(1-2)-b-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_164479,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_61,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 339
Nnalue NA, Lindberg AA "O-antigenic determinants in Salmonella species of serogroup C1 are expressed in distinct immunochemical populations of chains" -
Microbiology 143(2) (1997) 641-652
The O-antigenic specificities found among Salmonellae of serogroup C1 are O:6(1),7, O:6(2),7, O:6(1),6(2),7 and O:6,7,14, as defined by classical serology. Factor O:7 is the group-wide determinant while factors O:6(1), O:6(2) and O:14 are found in some strains but not others. Strains of the O:6(2),7 specificity are subject to lysogenic conversion by phages 6(1) and 14 to the O:6(1),7 and O:6,7,14 specificities, respectively. To further delineate antigenic complexity and serological relationships among strains of this serogroup monoclonal antibodies (mAbs) were generated against the O:6(1),6(2),7 polysaccharide of Salmonella thompson. Five mAbs of either the O:6(1) or O:6(2) specificities did not bind O:6,7,14 strains or LPS, showing that the O:6 determinant in these strains is neither O:6(1) nor O:6(2). Thus antigenic conversion of O:6(2),7 strains by phage 14 is accompanied by addition of O:14 as well as loss of O:6(2). Three mAbs which demonstrated group-wide reactivity, and were thus specific for O:7, recognized clearly by separable epitopes hereby defined as sub-specificities, O:7(1), O:7(2) and O:7(3). Immunoblotting of mAbs against electrophoretically resolved LPS showed that factors O:6(1) and O:6(2) are expressed only in LPS molecules of high molecular mass whereas O:7(2) and O:7(3) are expressed only in relatively low-molecular-mass chains. These results are consistent with the expression of different antigenic determinants in structurally distinct subpopulations of O chains. The implications of the existence of distinct subpopulation of chains is that the published structure of the O:6,7 repeat unit is not fully representative of the O-antigenic structure of this group
Salmonella LPS, LPS epitopes, O-antigenic complexity, O-antigen populations, antigenic conversionchain
NCBI PubMed ID: 9043141Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Department of Medical Microbiology, Faculty of Medicine & Health Sciences, United Arab Emirates University, PO Box 17666, Al Ain, United Arab Emirates, Karolinska Institute, Department of Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge Hospital, S-14186, Huddinge, Sweden
Methods: SDS-PAGE, ELISA, immunoblotting
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7. Compound ID: 1471
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a-D-Glcp2Ac-(1-2)-b-D-Manp-(1-4)-+
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-3)-a-D-GalpNAc-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
; n = 25
Compound class: S-layer glycoprotein
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_61,SB_72
The structure is contained in the following publication(s):
- Article ID: 467
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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8. Compound ID: 2629
Structure type: monomer
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_241118,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 896
Kondakova AN, Senchenkova SN, Gremyakov AI, Shashkov AS, Knirel YA, Fudala R, Kaca W "Structure of the O-specific polysaccharide of Proteus mirabilis O38 containing 2-acetamidoethyl phosphate and N-linked D-aspartic acid" -
Carbohydrate Research 338(22) (2003) 2387-2392
The O-antigen of Proteus mirabilis O38 was found to be unique among bacterial polysaccharides and to have the following structure: [carbohydrate structure in text] where D-Qui4N(Ac-D-Asp) is 4-(N-acetyl-D-aspart-4-ylamino)-4,6-dideoxy-D-glucose and AcEtnP is 2-acetamidoethyl phosphate. Neither of these entities have been hitherto found in natural polysaccharides. Structural studies were performed using 1D and 2D NMR spectroscopy, including experiments run in an H2O/D2O mixture to reveal correlations for NH protons. In addition, dephosphorylation, carboxyl reduction and selective cleavages were applied. Solvolysis of the polysaccharide with anhydrous HF gave an α-D-GlcNAc-(1→3)-D-Qui4N(Ac-D-Asp) disaccharide. Solvolysis with trifluoromethanesulfonic (triflic) acid afforded D-GlcNAc6(AcEtnP), thus showing the suitability of this reagent for the preparation of phosphorylated sugar derivatives.
Lipopolysaccharide, Proteus mirabilis, aspartic acid, O-Polysaccharide structure, serogroup classification
NCBI PubMed ID: 14572723Publication DOI: 10.1016/j.carres.2003.07.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, 93-232 Lodz, Poland
Methods: NMR, HF solvolysis, dephosphorylation, ESI-MS, carboxyl reduction, triflic acid solvolysis
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9. Compound ID: 3091
|
a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1--/spacer/ |
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Structure type: oligomer
Aglycon: spacer
Contained glycoepitopes: IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 1117
Pozsgay V "Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1" -
Journal of Organic Chemistry 63(17) (1998) 5983-5999
Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
synthesis, Oligosaccharides, antigens, Shigella dysenteriae type 1, Shigella dysenteriae, glycoconjugate vaccine, Schmidt's glycosylation
NCBI PubMed ID: 11672203Publication DOI: 10.1021/jo980660aJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: vipo@helix.nih.gov
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, 6 Center Dr. MSC 2720, Bethesda, MD, USA
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10. Compound ID: 3092
|
a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1--/spacer/ |
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Structure type: oligomer
Aglycon: spacer
Contained glycoepitopes: IEDB_125611,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 1117
Pozsgay V "Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1" -
Journal of Organic Chemistry 63(17) (1998) 5983-5999
Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
synthesis, Oligosaccharides, antigens, Shigella dysenteriae type 1, Shigella dysenteriae, glycoconjugate vaccine, Schmidt's glycosylation
NCBI PubMed ID: 11672203Publication DOI: 10.1021/jo980660aJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: vipo@helix.nih.gov
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, 6 Center Dr. MSC 2720, Bethesda, MD, USA
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11. Compound ID: 3093
|
a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1--/spacer/ |
Show graphically |
Structure type: oligomer
Aglycon: spacer
Contained glycoepitopes: IEDB_125611,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 1117
Pozsgay V "Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1" -
Journal of Organic Chemistry 63(17) (1998) 5983-5999
Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
synthesis, Oligosaccharides, antigens, Shigella dysenteriae type 1, Shigella dysenteriae, glycoconjugate vaccine, Schmidt's glycosylation
NCBI PubMed ID: 11672203Publication DOI: 10.1021/jo980660aJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: vipo@helix.nih.gov
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, 6 Center Dr. MSC 2720, Bethesda, MD, USA
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12. Compound ID: 3094
|
a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Glcp2Ac-(1-3)-a-L-Rhap-(1--/spacer/ |
Show graphically |
Structure type: oligomer
Aglycon: spacer
Contained glycoepitopes: IEDB_125611,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 1117
Pozsgay V "Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1" -
Journal of Organic Chemistry 63(17) (1998) 5983-5999
Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
synthesis, Oligosaccharides, antigens, Shigella dysenteriae type 1, Shigella dysenteriae, glycoconjugate vaccine, Schmidt's glycosylation
NCBI PubMed ID: 11672203Publication DOI: 10.1021/jo980660aJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: vipo@helix.nih.gov
Institutions: Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, 6 Center Dr. MSC 2720, Bethesda, MD, USA
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13. Compound ID: 3440
|
a-L-Rha-(1-3)-+
|
-4)-a-L-Rhap-(1-3)-b-D-Glcp?Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: sphingan
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_135849,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 1290
Yamazaki M, Thorne L, Mikolajczak M, Armentrout RW, Pollock TJ "Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88" -
Journal of Bacteriology 178 (1996) 2676-2687
Several structurally related capsular polysaccharides that are secreted by members of the genus Sphingomonas are being developed as aqueous rheological control agents for diverse industrial and food applications. They include gellan (S-60), welan (S-130), rhamsan (S-194), S-657, S-88, S-198, S-7, and NW-11. We refer to these polysaccharides as sphingans, after the genus name. This paper characterizes the first gene cluster isolated from a Sphingomonas species (S88) that is required for capsule synthesis. Overlapping DNA segments which spanned about 50 kbp of S88 DNA restored the synthesis of sphingan S-88 in capsule-negative mutants. The mutations were mapped into functional complementation groups, and the contiguous nucleotide sequence for the 29-kbp cluster was determined. The genetic complementation map and the DNA sequences were interpreted as an extended multicistronic locus containing genes essential for the assembly and secretion of polysaccharide S-88. Many of the deduced amino acid sequences were similar to gene products from other polysaccharide-secreting bacteria such as Rhizobium meliloti (succinoglycan), Xanthomonas campestris (xanthan gum), and Salmonella enterica (O antigen). The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans. Unexpectedly, there were also two genes for secretion of a lytic or toxin-like protein nested within the polysaccharide cluster. The conservation and linkage of genes that code for a defensive capsule and genes for secretion of an offensive lysin or toxin suggest a heretofore unknown pathogenic life history for Sphingomonas strain S88
biosynthesis, synthesis, gene, strain, polysaccharide, Sphingomonas, linkage, capsule
NCBI PubMed ID: 8626338Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Shin-Etsu Bio, Inc., San Diego, California 92121, USA
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14. Compound ID: 3498
|
a-L-Rha-(1-3)-+
|
-4)-a-L-Manp-(1-3)-b-D-Glcp?Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: sphingan
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_1394182,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 1290
Yamazaki M, Thorne L, Mikolajczak M, Armentrout RW, Pollock TJ "Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88" -
Journal of Bacteriology 178 (1996) 2676-2687
Several structurally related capsular polysaccharides that are secreted by members of the genus Sphingomonas are being developed as aqueous rheological control agents for diverse industrial and food applications. They include gellan (S-60), welan (S-130), rhamsan (S-194), S-657, S-88, S-198, S-7, and NW-11. We refer to these polysaccharides as sphingans, after the genus name. This paper characterizes the first gene cluster isolated from a Sphingomonas species (S88) that is required for capsule synthesis. Overlapping DNA segments which spanned about 50 kbp of S88 DNA restored the synthesis of sphingan S-88 in capsule-negative mutants. The mutations were mapped into functional complementation groups, and the contiguous nucleotide sequence for the 29-kbp cluster was determined. The genetic complementation map and the DNA sequences were interpreted as an extended multicistronic locus containing genes essential for the assembly and secretion of polysaccharide S-88. Many of the deduced amino acid sequences were similar to gene products from other polysaccharide-secreting bacteria such as Rhizobium meliloti (succinoglycan), Xanthomonas campestris (xanthan gum), and Salmonella enterica (O antigen). The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans. Unexpectedly, there were also two genes for secretion of a lytic or toxin-like protein nested within the polysaccharide cluster. The conservation and linkage of genes that code for a defensive capsule and genes for secretion of an offensive lysin or toxin suggest a heretofore unknown pathogenic life history for Sphingomonas strain S88
biosynthesis, synthesis, gene, strain, polysaccharide, Sphingomonas, linkage, capsule
NCBI PubMed ID: 8626338Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Shin-Etsu Bio, Inc., San Diego, California 92121, USA
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15. Compound ID: 3499
|
a-L-Manp-(1-3)-+
|
-4)-a-L-Rhap-(1-3)-b-D-Glcp2(50%)Ac-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: welan
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_135849,IEDB_136105,IEDB_1394182,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_189517,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 1290
Yamazaki M, Thorne L, Mikolajczak M, Armentrout RW, Pollock TJ "Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88" -
Journal of Bacteriology 178 (1996) 2676-2687
Several structurally related capsular polysaccharides that are secreted by members of the genus Sphingomonas are being developed as aqueous rheological control agents for diverse industrial and food applications. They include gellan (S-60), welan (S-130), rhamsan (S-194), S-657, S-88, S-198, S-7, and NW-11. We refer to these polysaccharides as sphingans, after the genus name. This paper characterizes the first gene cluster isolated from a Sphingomonas species (S88) that is required for capsule synthesis. Overlapping DNA segments which spanned about 50 kbp of S88 DNA restored the synthesis of sphingan S-88 in capsule-negative mutants. The mutations were mapped into functional complementation groups, and the contiguous nucleotide sequence for the 29-kbp cluster was determined. The genetic complementation map and the DNA sequences were interpreted as an extended multicistronic locus containing genes essential for the assembly and secretion of polysaccharide S-88. Many of the deduced amino acid sequences were similar to gene products from other polysaccharide-secreting bacteria such as Rhizobium meliloti (succinoglycan), Xanthomonas campestris (xanthan gum), and Salmonella enterica (O antigen). The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans. Unexpectedly, there were also two genes for secretion of a lytic or toxin-like protein nested within the polysaccharide cluster. The conservation and linkage of genes that code for a defensive capsule and genes for secretion of an offensive lysin or toxin suggest a heretofore unknown pathogenic life history for Sphingomonas strain S88
biosynthesis, synthesis, gene, strain, polysaccharide, Sphingomonas, linkage, capsule
NCBI PubMed ID: 8626338Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Shin-Etsu Bio, Inc., San Diego, California 92121, USA
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