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1. Compound ID: 54
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-6)-+
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b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-D-Gal |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_153529,IEDB_157001,IEDB_158533,IEDB_190606,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 16
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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2. Compound ID: 57
Structure type: oligomer
Trivial name: lacto-N-tetraose
Contained glycoepitopes: IEDB_117715,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_983931,SB_137,SB_145,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 16
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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3. Compound ID: 809
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a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-+
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-4)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: PS-Ib
Compound class: O-antigen, CPS
Contained glycoepitopes: IEDB_117715,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141589,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150899,IEDB_150933,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_241110,IEDB_983931,SB_116,SB_124,SB_127,SB_133,SB_137,SB_145,SB_156,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_174,SB_186,SB_187,SB_192,SB_195,SB_29,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 216
Watanabe M, Miyake K, Yanae K, Kataoka Y, Koizumi S, Endo T, Ozaki A, Iijima S "Molecular characterization of a novel b1,3-galactosyltransferase for capsular polysaccharide synthesis by Streptococcus agalactiae type Ib" -
Journal of Biochemistry 131(2) (2002) 183-191
A group B streptococcus, Streptococcus agalactiae type Ib, produces a high-molecular- weight polysaccharide consisting of the following pentasaccharide repeating unit: →4)-[α-D-NeupNAc-(2→3)-β-D-Galp-(1→3)-β-D-GlcpNAc-(1→3)]-β-D-Galp-(1→4)-β-D-Glcp-(1→. The type- specific capsular polysaccharide (CP) synthesis (cps) genes of this strain were cloned and analyzed. A cloned 10-kb DNA fragment contained cpsIbE to L and neu (neuraminic acid synthesis gene) B. Comparison of the gene products with those of S. agalactiae type Ia, which has a similar but distinct CP, showed that the translation products of cpsIa and cpsIb genes exhibited very high homology except for those of cpsJ and K. In the type Ia strain, cpsIaJ encodes β1,4- galactosyltransferase, which catalyzes the transfer of galactose as the fourth monosaccharide of the sugar repeating unit. In the type Ib CP, this galactose forms a β1,3-linkage to GlcNAc. The low homology between the type Ia and Ib CpsJs seems to reflect this difference. By enzymatic activity measurement, the cpsIbJ product was found to display β1,3-galactosyltransferase activity. Furthermore, hydrophobic cluster analysis clarified the similarities and differences of the structures in N-terminal regions, including the DXD motif, between the galactosyltransferases.
synthesis, transfer, structure, gene, DNA, strain, capsular, characterization, polysaccharide, Streptococcus, repeating unit, analysis, capsular polysaccharide, group, molecular, form, acid, type, high, group B Streptococcus, cluster, specific, neuraminic acid, activity, sugar, motif, region, translation, enzymatic, difference, fragment, pentasaccharide, galactose, comparison, biotechnology, cloned, Cluster Analysis, CPS, engineering, galactosyltransferase, Galactosyltransferases, homology, hydrophobic, Japan, measurement, monosaccharide, similarity, Streptococcus agalactiae
NCBI PubMed ID: 11820930Journal NLM ID: 0376600Publisher: Japanese Biochemical Society
Correspondence: miyake@proc.nubio.nagoya-u.ac.jp
Institutions: Department of Biotechnology, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
Methods: genetic methods
- Article ID: 1337
Zou W, Jennings HJ "Chemical-enzymatic synthesis of a branched hexasaccharide fragment of type Ia group B Streptococcus capsular polysaccharide" -
Journal of Carbohydrate Chemistry 15 (1996) 925-937
A branched hexasaccharide fragment of type Ia group B streptococcal polysaccharide, aNeuAc(2-3)bDGalp(1-4)bDGlcpNAc(1-3)[bDGlcp(1-4)]bDGalp(1-4)bDGlcpOMe (13) has been synthesised by chemical-enzymatic procedures.
synthesis, branched, hexasaccharide, capsular, polysaccharide, Streptococcus, capsular polysaccharide, group, type, group B Streptococcus, chemical, enzymatic, fragment, enzymatic synthesis
Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada
- Article ID: 1500
Cieslewicz MJ, Chaffin D, Glusman G, Kasper D, Madan A, Rodrigues S, Fahey J, Wessels MR, Rubens CE "Structural and genetic diversity of group B streptococcus capsular polysaccharides" -
Infection and Immunity 73(5) (2005) 3096-3103
Group B Streptococcus (GBS) is an important pathogen of neonates, pregnant women, and immunocompromised individuals. GBS isolates associated with human infection produce one of nine antigenically distinct capsular polysaccharides which are thought to play a key role in virulence. A comparison of GBS polysaccharide structures of all nine known GBS serotypes together with the predicted amino acid sequences of the proteins that direct their synthesis suggests that the evolution of serotype-specific capsular polysaccharides has proceeded through en bloc replacement of individual glycosyltransferase genes with DNA sequences that encode enzymes with new linkage specificities. We found striking heterogeneity in amino acid sequences of synthetic enzymes with very similar functions, an observation that supports horizontal gene transfer rather than stepwise mutagenesis as a mechanism for capsule variation. Eight of the nine serotypes appear to be closely related both structurally and genetically, whereas serotype VIII is more distantly related. This similarity in polysaccharide structure strongly suggests that the evolutionary pressure toward antigenic variation exerted by acquired immunity is counterbalanced by a survival advantage conferred by conserved structural motifs of the GBS polysaccharides
Bacterial Proteins, Streptococcus agalactiae, Bacterial Capsules, Genetic Variation
NCBI PubMed ID: 15845517Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: craig.rubens@seattlechildrens.org
Institutions: Division of Infectious Diseases, Children's Hospital, University of Washington, Seattle, WA 98109, USA, Channing Division of Infectious Diseases, Children's Hospital Boston, Department of Microbiology and Molecular Genetics, Harvard Medical School Boston, Massachusetts, Institute for Systems Biology and Division of Infectious Diseases, Children's Hospital, University of Washington, 3 Seattle, Washington
Methods: genetic methods, biosynthetic methods
- Article ID: 1751
Jennings HJ, Katzenellenbogen E, Lugowski C, Kasper DL "Structure of native polysaccharide antigens of type Ia and type Ib group B Streptococcus" -
Biochemistry 22 (1983) 1258-1264
NCBI PubMed ID: 6838851Publication DOI: 10.1021/bi00274a042Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, GC-MS
- Article ID: 2712
Schifferle RE, Jennings HJ, Wessels MR, Katzenellenbogen E, Roy R, Kasper DL "Immunochemical analysis of the types Ia and Ib group B streptococcal polysaccharides" -
Journal of Immunology 135 (1985) 4164-4170
The types Ia and Ib group B streptococcal type-specific polysaccharides have remarkable immunologic differences despite a great deal of structural similarity. Although these two complex polysaccharides differ only by a single glycosidic linkage, they are antigenically distinct. Furthermore, terminal sialic acid residues appear to be critical to the immunodeterminant on the type Ia polysaccharide, whereas the antigenicity of the type Ib polysaccharide does not show this dependence on sialic acid. In the current investigation we defined better the immunodeterminant of these polysaccharides. With homologous rabbit antiserum, the type Ia native and core polysaccharides demonstrated partial serologic identity, whereas the type Ib native and core polysaccharides demonstrated complete serologic identity. Surprisingly, the type I degalactosylated polysaccharide, degraded structure, was capable of reacting with a population of antibodies present in type Ia antiserum similar to the complete type Ia native polysaccharide, although demonstrating a reduced level of immunodeterminant expression. Unlike the reactions of the type Ia polysaccharides with homologous rabbit antiserum, the Ib native and core polysaccharides were able to react with identical populations of antibodies in type Ib-specific antiserum. A minor population of antibodies was demonstrated in the type Ib antiserum, which was reactive with the degalactosylated polysaccharide. That a population of antibodies reactive toward the degalactosylated polysaccharide is present in both type Ia and type Ib antisera suggests that the Iabc cross-reacting determinant is due to the presence of serum antibodies reactive with this trisaccharide repeating unit, which is shared by both the type Ia and the type Ib native and core polysaccharides.
NCBI PubMed ID: 3934276Journal NLM ID: 2985117RPublisher: Bethesda, MD: American Association of Immunologists
Methods: serological methods
- Article ID: 4049
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- 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: 17009947Publication DOI: 10.1134/S000629790609001XJournal NLM ID: 0376536Publisher: 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
- Article ID: 4727
Stowell SR, Arthur CM, McBride R, Berger O, Razi N, Heimburg-Molinaro J, Rodrigues LC, Gourdine J, Noll AJ, von Gunten S, Smith DF, Knirel YA, Paulson JC, Cummings RD "Microbial glycan microarrays define key features of host-microbial interactions" -
Nature Chemical Biology 10(6) (2014) 470-476
Genomic approaches continue to provide unprecedented insight into the microbiome, yet host immune interactions with diverse microbiota can be difficult to study. We therefore generated a microbial microarray containing defined antigens isolated from a broad range of microbial flora to examine adaptive and innate immunity. Serological studies with this microarray show that immunoglobulins from multiple mammalian species have unique patterns of reactivity, whereas exposure of animals to distinct microbes induces specific serological recognition. Although adaptive immunity exhibited plasticity toward microbial antigens, immunological tolerance limits reactivity toward self. We discovered that several innate immune galectins show specific recognition of microbes that express self-like antigens, leading to direct killing of a broad range of Gram-negative and Gram-positive microbes. Thus, host protection against microbes seems to represent a balance between adaptive and innate immunity to defend against evolving antigenic determinants while protecting against molecular mimicry.
molecular mimicry, glycan, interaction, Gram-negative, galectins, Gram-positive, innate immunity, Glycomics
Publication DOI: 10.1038/nchembio.1525Journal NLM ID: 101231976Publisher: New York, NY: Nature Publishing Group
Correspondence: jpaulson@scripps.edu; rdcummi@emory.edu
Institutions: Department of Biochemistry and the Glycomics Center, Emory University School of Medicine, Atlanta, Georgia, USA, Department of Cell and Molecular Biology, The Scripps Research Institute, La Jolla, California, USA, Department of and Chemical Physiology, The Scripps Research Institute, La Jolla, California, USA
Methods: serological methods
- Article ID: 4835
Berti F, Ravenscroft N "Characterization of Carbohydrate Vaccines by NMR Spectroscopy" -
Methods in Molecular Biology 1331 (2015) 189-209
Physicochemical techniques are a powerful tool for the structural characterization of carbohydrate-based vaccines. High-field Nuclear Magnetic Resonance (NMR) spectroscopy has been established as an extremely useful and robust method for tracking the industrial manufacturing process of these vaccines from polysaccharide bulk antigen through to the final formulation. Here, we describe the use of proton NMR for structural identity and conformity testing of carbohydrate-based vaccines.
carbohydrates, capsular polysaccharide, antigens, nuclear magnetic resonance spectroscopy, vaccines
NCBI PubMed ID: 26169742Publication DOI: 10.1007/978-1-4939-2874-3_12Journal NLM ID: 9214969Publisher: Springer
Correspondence: francesco.x.berti@gsk.com
Institutions: Research, GSK Vaccines, Via Fiorentina 1, 53100, Siena, Italy
- Article ID: 5420
Del Bino L, Calloni I, Oldrini D, Raso MM, Cuffaro R, Arda A, Codee JDC, Jiménez-Barbero J, Adamo R "Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides" -
Chemistry: a European Journal 25(71) (2019) 16277-16278
Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and differ only in the connection of the Neu5Ac α2-3 Gal side chain to the GlcNAc unit, which is a β1-4 linkage in serotype Ia and a β1-3 linkage in serotype Ib. The development of efficient regioselective routes for GlcNAc β1-3 [Glc β1-4]Gal synthons is described, which give access to different group B Streptococcus (GBS) Ia and Ib repeating unit frameshifts. These glycans were used to probe the conformation and molecular dynamics of the two polysaccharides, highlighting the different presentation of the protruding Neu5Ac α2-3 Gal moieties on the polysaccharide backbones and a higher flexibility of Ib polymer relative to Ia, which can impact epitope exposure.
conformation, synthesis, carbohydrates, Streptococcus, glycan, conformation analysis, glycosylation, regioselectivity, therapeutics
NCBI PubMed ID: 31506992Publication DOI: 10.1002/chem.201903527Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: roberto.x.adamo@gsk.com
Institutions: GSK, Via Fiorentina 1, 53100, Siena, Italy, CIC bioGUNE, Bizkaia Technology Park, Building 800, 48160, Derio, Spain, Department of Bioorganic Synthesis, Leiden University, 2333, Leiden, The Netherlands, Basque Foundation for Science IKERBASQUE, Bilbao, Spain, Department of Organic Chemistry II, Faculty of Science and Technology, University of the Basque Country, 48940, Leioa, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, MD simulations, UV, optical rotation measurement, ESI-HR-MS, flash chromatography, conformational analysis
- Article ID: 5440
Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Structure determination of Streptococcus suis serotypes 7 and 8 capsular polysaccharides and assignment of functions of the cps locus genes involved in their biosynthesis" -
Carbohydrate Research 473 (2019) 36-45
Streptococcus suis serotypes 7 and 8 are counted among the top six S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on these serotypes. Since S. suis serotyping system is based upon capsular polysaccharide (CPS) antigenicity and the CPS is considered a major virulence factor for encapsulated pathogens, here we determined for the first time the chemical compositions and structures of serotypes 7 and 8 CPSs. Chemical and spectroscopic data gave the following repeating unit sequences: [3)L-Rha(α1-P-2)D-Gal(α1-4)D-GlcA(β1-3)D-FucNAc4N(α1-]n for serotype 7 and [2)L-Rha(α1-P-4)D-ManNAc(β1-4)D-Glc(α1-]n for serotype 8. As serotype 8 CPS is identical to Streptococcus pneumoniae type 19F CPS, dot-blot analyses showed a strong reaction of the 19F polysaccharide with reference anti-S. suis serotype 8 rabbit serum. A correlation between S. suis serotypes 7 and 8 sequences and genes of those serotypes' loci encoding putative glycosyltransferases and polymerases responsible for the biosynthesis of the repeating units was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of the disease caused by S. suis serotypes 7 and 8.
capsular polysaccharide, carbohydrate structure, Serotype 8, Streptococcus suis, Serotype 7
NCBI PubMed ID: 30605786Publication DOI: 10.1016/j.carres.2018.12.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Segura
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, GLC-MS, sugar analysis, 31P NMR, acid hydrolysis, Western blotting, bioinformatic analysis
- Article ID: 5485
Paoletti LC, Kasper DL "Surface Structures of Group B Streptococcus Important in Human Immunity" -
Microbiology Spectrum 7(2) (2019) ID GPP3-0001-2017
The surface of the Gram-positive opportunistic pathogen Streptococcus agalactiae, or group B Streptococcus (GBS), harbors several carbohydrate and protein antigens with the potential to be effective vaccines. Capsular polysaccharides of all clinically-relevant GBS serotypes coupled to immunogenic proteins of both GBS and non-GBS origin have undergone extensive testing in animals that led to advanced clinical trials in healthy adult women. In addition, GBS proteins either alone or in combination have been tested in animals; a fusion protein construct has recently advanced to human clinical studies. Given our current understanding of the antigenicity and immunogenicity of the wide array of GBS surface antigens, formulations now exist for the generation of viable vaccines against diseases caused by GBS.
structure, capsular polysaccharides, group B Streptococcus, surface, vaccines, Streptococcus agalactiae, Gram-positive
NCBI PubMed ID: 30873933Publication DOI: 10.1128/microbiolspec.GPP3-0001-2017Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: Lawrence C. Paoletti
Institutions: Division of Immunology, Department of Microbiology and Immunobiology, Harvard Medical School, Boston, MA 02115
- 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: 6051
Duke JA, Paschall AV, Robinson LS, Knoot CJ, Vinogradov E, Scott NE, Feldman MF, Avci FY, Harding CM "Development and Immunogenicity of a Prototype Multivalent Group B Streptococcus Bioconjugate Vaccine" -
ACS Infectious Diseases 7(11) (2021) 3111-3123
Group B Streptococcus (GBS) is a leading cause of neonatal infections and invasive diseases in nonpregnant adults worldwide. Developing a protective conjugate vaccine targeting the capsule of GBS has been pursued for more than 30 years; however, it has yet to yield a licensed product. In this study, we present a novel bioconjugation platform for producing a prototype multivalent GBS conjugate vaccine and its subsequent analytical and immunological characterizations. Using a glycoengineering strategy, we generated strains of Escherichia coli that recombinantly express the type Ia, type Ib, and type III GBS capsular polysaccharides. We then combined the type Ia-, Ib-, and III-capsule-expressing E. coli strains with an engineered Pseudomonas aeruginosa exotoxin A (EPA) carrier protein and the PglS oligosaccharyltransferase. Coexpression of a GBS capsule, the engineered EPA protein, and PglS enabled the covalent attachment of the target GBS capsule to an engineered serine residue on EPA, all within the periplasm of E. coli. GBS bioconjugates were purified, analytically characterized, and evaluated for immunogenicity and functional antibody responses. This proof-of-concept study signifies the first step in the development of a next-generation multivalent GBS bioconjugate vaccine, which was validated by the production of conjugates that are able to elicit functional antibodies directed against the GBS capsule.
group B Streptococcus, capsule, conjugate vaccine, bioconjugation, bioconjugate, multivalent
NCBI PubMed ID: 34633812Publication DOI: 10.1021/acsinfecdis.1c00415Journal NLM ID: 101654580Publisher: Washington, DC: American Chemical Society
Correspondence: Fikri Y. Avci
; Christian M. Harding
Institutions: Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA, USA, United States, Center for Molecular Medicine, University of Georgia, Athens, GA, USA, United States, VaxNewMo, St. Louis, Missouri 63110, United States, Human Health Therapeutics Centre, National Research Council Canada, Ottawa, ON K1A 0R6, Canada, Department of Microbiology and Immunology, University of Melbourne at the Peter Doherty Institute for Infection and Immunity, Parkville, Australia, Department of Molecular Microbiology, Washington University School of Medicine, St. Louis, Missouri 63110, United States
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ELISA, ESI-MS, Western blotting, HPLC, SEC, immunization, protein detection, opsonophagocytosis assay, glycoengineering, bioconjugation
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4. Compound ID: 1445
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D-Asp2Ac-(4-4)-b-D-Quip4N-(1-6)-+
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-6)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-6)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 459
Torzewska A, Kocharova NA, Zatonsky GV, Blaszczyk A, Bystrova OV, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-polysaccharide and serological cross-reactivity of the Providencia stuartii O33 lipopolysaccharide containing 4-(N-acetyl-D-aspart-4-yl)amino-4,6-dideoxy-D-glucose" -
FEMS Immunology and Medical Microbiology 41(2) (2004) 133-139
The O-polysaccharide of Providencia stuartii O33 was obtained by mild acid degradation of the lipopolysaccharide and the following structure of the tetrasaccharide repeating unit was established: →6)-α-D-GlcpNAc-(1→4)-α-D-GalpA-(1→3)-α-D-GlcpNAc-(1→3)-β-D-Quip4N(Ac-D-Asp)-(1→, where d-Qui4N(Ac-D-Asp) is 4-(N-acetyl-D-aspart-4-yl)amino-4,6-dideoxy-D-glucose. Structural studies were performed using sugar and methylation analyses and NMR spectroscopy, including conventional 2D 1H, 1H COSY, TOCSY, NOESY and 1H, 13C HSQC experiments as well as COSY and NOESY experiments in an H2O-D2O mixture to reveal correlations for NH protons. The O-polysaccharide of P. stuartii O33 shares an α-D-GlcpNAc-(1→3)-β-D-Quip4N(Ac-D-Asp) epitope with that of Proteus mirabilis O38, which seems to be responsible for a marked serological cross-reactivity of anti-P. stuartii O33 serum with the lipopolysaccharide of the latter bacterium. P. stuartii O33 is serologically related also to P. stuartii O4, whose O-polysaccharide contains a lateral β-D-Qui4N(Ac-L-Asp) residue.
Lipopolysaccharide, O-antigen, bacterial polysaccharide structure, serological relationship, Providencia stuartii
NCBI PubMed ID: 15145457Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16,90-237 Lodz, Poland
Methods: NMR-2D, methylation, NMR
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5. Compound ID: 1612
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L-Asp2Ac-(4-4)-b-D-Quip4N-(1-6)-+
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-3)-b-D-Galp-(1-6)-b-D-GlcpNAc-(1-6)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 498
Kocharova NA, Senchenkova SN, Kondakova AN, Gremyakov AI, Zatonsky GV, Shashkov AS, Knirel YA, Kochetkov NK "D- And L-aspartic acids: new non-sugar components of bacterial polysaccharides" -
Biochemistry (Moscow) 69(1) (2004) 103-107
For the first time in bacterial polysaccharides, residues of D- and L-aspartic acids were identified as N-acyl substituents of 4-amino-4,6-dideoxy-D-glucose in the O-antigens of enterobacteria of the genera Providencia and Proteus.
Lipopolysaccharide, NMR, LPS, structure, Bacterial, structural, polysaccharide, O-antigen, polysaccharides, O antigen, acidic, acidic polysaccharide, acid, phosphate, bacteria, O-specific, O-specific polysaccharide, Providencia, Proteus, Proteus mirabilis, serological, Ethanolamine phosphate, Bacterial polysaccharide, component, bacterial polysaccharides, amino acid, PDF, aspartic acid, N-linked, Acids
NCBI PubMed ID: 14972025Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR-2D, methylation, NMR, HF solvolysis, ESI-MS, Smith degradation, triflic acid solvolysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4588
Ovchinnikova OG, Rozalski A, Liu B, Knirel YA "O-Antigens of bacteria of the genus Providencia: structure, serology, genetics, and biosynthesis" -
Biochemistry (Moscow) 78(7) (2013) 798-817
The genus Providencia consists of eight species of opportunistic pathogenic enterobacteria that can cause enteric diseases and urinary tract infections. The existing combined serological classification scheme of three species, P. alcalifaciens, P. stuartii, and P. rustigianii, is based on the specificity of O-antigens (O-polysaccharides) and comprises 63 O-serogroups. Differences between serogroups are related to polymorphism at a specific genome locus, the O-antigen gene cluster, responsible for O-antigen biosynthesis. This review presents data on structures of 36 O-antigens of Providencia, many of which contain unusual monosaccharides and non-carbohydrate components. The structural data correlate with the immunospecificity of the O-antigens and enable substantiation on a molecular level of serological relationships within the genus Providencia and between strains of Providencia and bacteria of the genera Proteus, Escherichia, and Salmonella. Peculiar features of the O-antigen gene cluster organization in 10 Providencia serogroups and biosynthetic pathways of nucleotide precursors of specific monosaccharide components of the O-antigens also are discussed.
Lipopolysaccharide, biosynthesis, O-antigen, gene cluster, Providencia, serological specificity
NCBI PubMed ID: 24010842Publication DOI: 10.1134/S0006297913070110Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: olga.ovchinnikova@gmail.com
Institutions: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, PL 90-237 Lodz, Poland, TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 Hongda Street, TEDA, 300457 Tianjin, P. R. China
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6. Compound ID: 1755
|
L-Asp2Ac-(1-4)-b-D-Quip4N-(1-6)-+
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-3)-b-D-Galp-(1-6)-b-D-GlcpNAc-(1-6)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 544
Kocharova NA, Torzewska A, Zatonsky GV, Blaszczyk A, Bystrova OV, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-polysaccharide of Providencia stuartii O4 containing 4-(N-acetyl-L-aspart-4-yl)amino-4,6-dideoxy-D-glucose" -
Carbohydrate Research 339(2) (2004) 195-200
The O-polysaccharide of Providencia stuartii O4 was obtained by mild acid degradation of the lipopolysaccharide, and the following structure of the pentasaccharide repeating unit was established: [structure: see text] where D-Qui4N(L-AspAc) is 4-(N-acetyl-L-aspart-4-yl)amino-4,6-dideoxy-D-glucose, which has not been hitherto found in bacterial polysaccharides. Structural studies were performed using sugar and methylation analyses, Smith degradation and NMR spectroscopy, including conventional 2D 1H,1H COSY, TOCSY, NOESY and 1H,13C HSQC experiments as well as COSY and NOESY experiments run in an H(2)O-D(2)O mixture to reveal correlations for NH protons.
Lipopolysaccharide, O-polysaccharide, bacterial polysaccharide structure, Providencia stuartii
NCBI PubMed ID: 14698876Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis, Smith degradation
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7. Compound ID: 2315
|
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-+
|
Cho-(1--P--6)--+ | a-Kdop-(2-4)-+ P-4)-+
| | | |
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_117715,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_135394,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_150908,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_137,SB_145,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 786
Cox AD, Howard MD, Brisson JR, van der Zwan M, Thibault P, Perry MB, Inzana TJ "Structural analysis of the phase-variable lipooligosaccharide from Haemophilus somnus strain 738" -
European Journal of Biochemistry 253(2) (1998) 507-516
The structure of the phase variable lipooligosaccharide (LOS) from Haemophilus somnus strain 738 was elucidated. The LOS was subjected to a variety of degradative procedures. The structures of the purified products were established by monosaccharide and methylation analyses, NMR spectroscopy and mass spectrometry. The following structures for the two major components were determined on the basis of the combined data from these experiments. [structure in text]. In the structures Kdo is 3-deoxy-D-manno-octulosonic acid, PEtn is phosphoethanolamine, PCho is phosphocholine, Hep is L-glycero-D-manno-heptose, and the remaining glucose units have the D configuration. The elucidation of these structures has increased our understanding of the relationship between the phase-variable LOS and the pathogenic potential of this organism.
NMR, Haemophilus, Phase variation, Lipooligosaccharide, strain, structural, analysis, structural analysis, Haemophilus somnus, nanoelectrospray mass spectrometry
NCBI PubMed ID: 9654104Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: andrew.cox@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Centre for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg VA, USA
Methods: methylation, NMR, sugar analysis, MS, chemical degradation
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8. Compound ID: 2316
|
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-+
|
Cho-(1--P--6)--+ | a-Kdop-(2-4)-+ P-4)-+
| | | |
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_135394,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_150908,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 786
Cox AD, Howard MD, Brisson JR, van der Zwan M, Thibault P, Perry MB, Inzana TJ "Structural analysis of the phase-variable lipooligosaccharide from Haemophilus somnus strain 738" -
European Journal of Biochemistry 253(2) (1998) 507-516
The structure of the phase variable lipooligosaccharide (LOS) from Haemophilus somnus strain 738 was elucidated. The LOS was subjected to a variety of degradative procedures. The structures of the purified products were established by monosaccharide and methylation analyses, NMR spectroscopy and mass spectrometry. The following structures for the two major components were determined on the basis of the combined data from these experiments. [structure in text]. In the structures Kdo is 3-deoxy-D-manno-octulosonic acid, PEtn is phosphoethanolamine, PCho is phosphocholine, Hep is L-glycero-D-manno-heptose, and the remaining glucose units have the D configuration. The elucidation of these structures has increased our understanding of the relationship between the phase-variable LOS and the pathogenic potential of this organism.
NMR, Haemophilus, Phase variation, Lipooligosaccharide, strain, structural, analysis, structural analysis, Haemophilus somnus, nanoelectrospray mass spectrometry
NCBI PubMed ID: 9654104Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: andrew.cox@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Centre for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg VA, USA
Methods: methylation, NMR, sugar analysis, MS, chemical degradation
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9. Compound ID: 2317
|
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-D-manHep |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_117715,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_140087,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_2189047,IEDB_983931,SB_137,SB_145,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 786
Cox AD, Howard MD, Brisson JR, van der Zwan M, Thibault P, Perry MB, Inzana TJ "Structural analysis of the phase-variable lipooligosaccharide from Haemophilus somnus strain 738" -
European Journal of Biochemistry 253(2) (1998) 507-516
The structure of the phase variable lipooligosaccharide (LOS) from Haemophilus somnus strain 738 was elucidated. The LOS was subjected to a variety of degradative procedures. The structures of the purified products were established by monosaccharide and methylation analyses, NMR spectroscopy and mass spectrometry. The following structures for the two major components were determined on the basis of the combined data from these experiments. [structure in text]. In the structures Kdo is 3-deoxy-D-manno-octulosonic acid, PEtn is phosphoethanolamine, PCho is phosphocholine, Hep is L-glycero-D-manno-heptose, and the remaining glucose units have the D configuration. The elucidation of these structures has increased our understanding of the relationship between the phase-variable LOS and the pathogenic potential of this organism.
NMR, Haemophilus, Phase variation, Lipooligosaccharide, strain, structural, analysis, structural analysis, Haemophilus somnus, nanoelectrospray mass spectrometry
NCBI PubMed ID: 9654104Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: andrew.cox@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Centre for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg VA, USA
Methods: methylation, NMR, sugar analysis, MS, chemical degradation
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10. Compound ID: 2318
|
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-L-gro-D-manHep |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140087,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_2189047,IEDB_983931,SB_137,SB_156,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 786
Cox AD, Howard MD, Brisson JR, van der Zwan M, Thibault P, Perry MB, Inzana TJ "Structural analysis of the phase-variable lipooligosaccharide from Haemophilus somnus strain 738" -
European Journal of Biochemistry 253(2) (1998) 507-516
The structure of the phase variable lipooligosaccharide (LOS) from Haemophilus somnus strain 738 was elucidated. The LOS was subjected to a variety of degradative procedures. The structures of the purified products were established by monosaccharide and methylation analyses, NMR spectroscopy and mass spectrometry. The following structures for the two major components were determined on the basis of the combined data from these experiments. [structure in text]. In the structures Kdo is 3-deoxy-D-manno-octulosonic acid, PEtn is phosphoethanolamine, PCho is phosphocholine, Hep is L-glycero-D-manno-heptose, and the remaining glucose units have the D configuration. The elucidation of these structures has increased our understanding of the relationship between the phase-variable LOS and the pathogenic potential of this organism.
NMR, Haemophilus, Phase variation, Lipooligosaccharide, strain, structural, analysis, structural analysis, Haemophilus somnus, nanoelectrospray mass spectrometry
NCBI PubMed ID: 9654104Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: andrew.cox@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Centre for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg VA, USA
Methods: methylation, NMR, sugar analysis, MS, chemical degradation
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11. Compound ID: 2359
|
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-+
|
Cho-(1--P--6)--+ | a-Kdop-(2-4)-+
| | |
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_117715,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_137,SB_145,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 819
Howard MD, Cox AD, Weiser JN, Schurig GG, Inzana TJ "Antigenic diversity of Haemophilus somnus lipooligosaccharide: Phase-variable accessibility of the phosphorylcholine epitope" -
Journal of Clinical Microbiology 38(12) (2000) 4412-4419
The lipooligosaccharide (LOS) of Haemophilus somnus undergoes antigenic phase variation, which may facilitate evasion from the bovine host immune response and/or colonization and dissemination. However, LOS antigenic diversity in H. somnus has not been adequately investigated. In this study, monoclonal antibodies (MAbs) specific to various LOS epitopes were used to investigate antigenic variation and stability in LOS from H. somnus strains and phase variants. Clinical isolates of H. somnus exhibited intrastrain, as well as interstrain, antigenic heterogeneity in LOS when probed with MAbs to outer core oligosaccharide epitopes in an enzyme-linked immunosorbent assay (ELISA). However, epitopes reactive with MAbs directed predominately to the inner core heptose region were highly conserved. At least one epitope, which was expressed in few strains, was identified. One LOS component affected by phase variation was identified as phosphorylcholine (PCho), which is linked to the primary glucose residue. Inhibition ELISA, immunoblotting, and electrospray-mass spectrometry were used to confirm that MAb 5F5.9 recognized PCho. LOS reactivity with MAb 5F5.9 was associated with loss of most of the outer core oligosaccharide, indicating that reactivity with PCho was affected by phase variation of the glycose residues in this region. Our results indicate that outer core epitopes of H. somnus LOS exhibit a high degree of random, phase-variable antigenic heterogeneity and that such heterogeneity must be considered in the design of vaccines and diagnostic tests.
Haemophilus, Lipooligosaccharide, antigenic, epitope, phosphorylcholine, Haemophilus somnus, diversity
NCBI PubMed ID: 11101573Journal NLM ID: 7505564Publisher: American Society for Microbiology
Institutions: Center for Molecular Medicine and Infectious Diseases, Virginia-Maryland Regional College of Veterinary Medicine, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6, Canada, Departments of Pediatrics and Microbiology, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 191043
Methods: SDS-PAGE, ELISA, ESI-MS, MS, de-O-acetylation, immunoblotting, statistical analysis, inhibited ELISA
- Article ID: 1459
Holst O "Chemical structure of the core region of lipopolysaccharides - an update" -
Trends in Glycoscience and Glycotechnology 14(76) (2002) 87-103
Lipopolysaccharides (LPS) are the endotoxins of Gram-negative bacteria and very well known for their immunological, pharmacological and pathophysiological effects displayed in eucaryotic cells and organisms. To date, much emphasis has been put on the elucidation of the chemical structures of LPS and on their relation, or that of substructures, to the various biological effects. The lipid part of LPS, the lipid A, was proven to represent the toxic principle of endotoxin. However, lipid A toxicity depends strongly on its structure, and is influenced by a second region of LPS, the core region, that is covalently linked to lipid A. Also, the core region possesses immunogenic properties. Therefore, complete structural analyses of the core region and the comparison of its structures with biological features of LPS are of high importance for a better understanding of LPS action, and one prerequesite for strategies aimed at the treatment of endotoxicosis. In the past, quite a number of structures of the core regions from various Gram-negative bacteria were published and summarized in several overviews. The present review adds to this knowledge those structures that were published between October 1998 and December 2001.
lipopolysaccharides, heptose, Kdo, chemical structure, core region, tructure
Publication DOI: 10.4052/tigg.14.87Journal NLM ID: 9425898Correspondence: oholst@fz-borstel.de
Institutions: Structural Biochemistry, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
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12. Compound ID: 3625
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a-L-Fucp-(1-4)-+
|
b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-Glcp-(1--/acetylphenylenediamine-HSA/ |
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Structure type: oligomer
Aglycon: acetylphenylenediamine-HSA
Trivial name: Lewis a antigen determinant
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_117715,IEDB_130653,IEDB_135511,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141499,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_157001,IEDB_174333,IEDB_190606,IEDB_226432,IEDB_423096,IEDB_461723,IEDB_983931,SB_137,SB_145,SB_155,SB_156,SB_160,SB_161,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1358
Appelmelk BJ, Simoons-Smit I, Negrini R, Moran AP, Aspinall GO, Forte JG, de Vries T, Quan H, Verboom T, Maaskant JJ, Ghiara P, Kuipers EJ, Bloemena E, Tadema TM, Townsend RR, Tyagarajan K, Crothers JM, Monteiro MA, Savio A, De Graaf J "Potential role of molecular mimicry between Helicobacter pylori lipopolysaccharide and host Lewis blood group antigens in autoimmunity" -
Infection and Immunity 64 (1996) 2031-2040
Helicobacter pylori is involved in gastritis, gastric and duodenal ulcers, gastric adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma. Earlier studies already suggested a role for autoimmune phenomena in H. pylori-linked disease. We now report that lipopolysaccharides (LPS) of H. pylori express Lewis y, Lewis x, and H type I blood group structures similar to those commonly occurring in gastric mucosa. Immunization of mice and rabbits with H. pylori cells or purified LPS induced an anti-Lewis x or y or anti-H type I response, yielding antibodies that bound human and murine gastric glandular tissue, granulocytes, adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma cells. Experimental oral infections in mice or natural infection in humans yielded anti-Lewis antibodies also. The beta chain of gastric (H+,K+)-ATPase, the parietal cell proton pump involved in acid secretion, contained Lewis y epitopes; gastric mucin contained Lewis x and y antigenic determinants. Growth in mice of a hybridoma that secretes H. pylori-induced anti-Lewis y monoclonal antibodies resulted in histopathological evidence of gastritis, which indicates a direct pathogenic role for anti-Lewis antibodies. In conclusion, our observations demonstrate that molecular mimicry between H. pylori LPS and the host, based on Lewis antigens, and provide understanding of an autoimmune mechanism for H. pylori-associated type B gastritis.
Lipopolysaccharide, antigen, LPS, potential, molecular mimicry, Helicobacter pylori, S-type LPS, Lewis x, blood group antigens
NCBI PubMed ID: 8675304Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amsterdam, The Netherlands
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13. Compound ID: 3626
|
a-L-Fucp-(1-4)-+
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a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-Glcp-(1--/acetylphenylenediamine-HSA/ |
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Structure type: oligomer
Aglycon: acetylphenylenediamine-HSA
Trivial name: Lewis b antigen determinant
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_117715,IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135511,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141499,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_142489,IEDB_143248,IEDB_143249,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149556,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_157001,IEDB_174333,IEDB_190606,IEDB_226432,IEDB_423095,IEDB_423096,IEDB_461709,IEDB_461719,IEDB_461723,IEDB_461724,IEDB_983931,SB_100,SB_137,SB_145,SB_146,SB_150,SB_153,SB_154,SB_155,SB_156,SB_160,SB_161,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1358
Appelmelk BJ, Simoons-Smit I, Negrini R, Moran AP, Aspinall GO, Forte JG, de Vries T, Quan H, Verboom T, Maaskant JJ, Ghiara P, Kuipers EJ, Bloemena E, Tadema TM, Townsend RR, Tyagarajan K, Crothers JM, Monteiro MA, Savio A, De Graaf J "Potential role of molecular mimicry between Helicobacter pylori lipopolysaccharide and host Lewis blood group antigens in autoimmunity" -
Infection and Immunity 64 (1996) 2031-2040
Helicobacter pylori is involved in gastritis, gastric and duodenal ulcers, gastric adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma. Earlier studies already suggested a role for autoimmune phenomena in H. pylori-linked disease. We now report that lipopolysaccharides (LPS) of H. pylori express Lewis y, Lewis x, and H type I blood group structures similar to those commonly occurring in gastric mucosa. Immunization of mice and rabbits with H. pylori cells or purified LPS induced an anti-Lewis x or y or anti-H type I response, yielding antibodies that bound human and murine gastric glandular tissue, granulocytes, adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma cells. Experimental oral infections in mice or natural infection in humans yielded anti-Lewis antibodies also. The beta chain of gastric (H+,K+)-ATPase, the parietal cell proton pump involved in acid secretion, contained Lewis y epitopes; gastric mucin contained Lewis x and y antigenic determinants. Growth in mice of a hybridoma that secretes H. pylori-induced anti-Lewis y monoclonal antibodies resulted in histopathological evidence of gastritis, which indicates a direct pathogenic role for anti-Lewis antibodies. In conclusion, our observations demonstrate that molecular mimicry between H. pylori LPS and the host, based on Lewis antigens, and provide understanding of an autoimmune mechanism for H. pylori-associated type B gastritis.
Lipopolysaccharide, antigen, LPS, potential, molecular mimicry, Helicobacter pylori, S-type LPS, Lewis x, blood group antigens
NCBI PubMed ID: 8675304Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amsterdam, The Netherlands
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14. Compound ID: 3630
|
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-Glcp-(1--/acetylphenylenediamine-HSA/ |
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Structure type: oligomer
Aglycon: acetylphenylenediamine-HSA
Trivial name: H type I antigen
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_117715,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_142489,IEDB_143249,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_157001,IEDB_174333,IEDB_190606,IEDB_423095,IEDB_461709,IEDB_461719,IEDB_983931,SB_100,SB_137,SB_145,SB_153,SB_154,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1358
Appelmelk BJ, Simoons-Smit I, Negrini R, Moran AP, Aspinall GO, Forte JG, de Vries T, Quan H, Verboom T, Maaskant JJ, Ghiara P, Kuipers EJ, Bloemena E, Tadema TM, Townsend RR, Tyagarajan K, Crothers JM, Monteiro MA, Savio A, De Graaf J "Potential role of molecular mimicry between Helicobacter pylori lipopolysaccharide and host Lewis blood group antigens in autoimmunity" -
Infection and Immunity 64 (1996) 2031-2040
Helicobacter pylori is involved in gastritis, gastric and duodenal ulcers, gastric adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma. Earlier studies already suggested a role for autoimmune phenomena in H. pylori-linked disease. We now report that lipopolysaccharides (LPS) of H. pylori express Lewis y, Lewis x, and H type I blood group structures similar to those commonly occurring in gastric mucosa. Immunization of mice and rabbits with H. pylori cells or purified LPS induced an anti-Lewis x or y or anti-H type I response, yielding antibodies that bound human and murine gastric glandular tissue, granulocytes, adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma cells. Experimental oral infections in mice or natural infection in humans yielded anti-Lewis antibodies also. The beta chain of gastric (H+,K+)-ATPase, the parietal cell proton pump involved in acid secretion, contained Lewis y epitopes; gastric mucin contained Lewis x and y antigenic determinants. Growth in mice of a hybridoma that secretes H. pylori-induced anti-Lewis y monoclonal antibodies resulted in histopathological evidence of gastritis, which indicates a direct pathogenic role for anti-Lewis antibodies. In conclusion, our observations demonstrate that molecular mimicry between H. pylori LPS and the host, based on Lewis antigens, and provide understanding of an autoimmune mechanism for H. pylori-associated type B gastritis.
Lipopolysaccharide, antigen, LPS, potential, molecular mimicry, Helicobacter pylori, S-type LPS, Lewis x, blood group antigens
NCBI PubMed ID: 8675304Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amsterdam, The Netherlands
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15. Compound ID: 4064
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a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-+
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-6)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_117715,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143794,IEDB_146100,IEDB_146664,IEDB_149138,IEDB_149139,IEDB_149141,IEDB_149174,IEDB_150899,IEDB_150933,IEDB_151531,IEDB_157001,IEDB_190606,IEDB_241110,IEDB_983931,SB_116,SB_124,SB_127,SB_133,SB_137,SB_145,SB_156,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_174,SB_186,SB_187,SB_192,SB_195,SB_29,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 1500
Cieslewicz MJ, Chaffin D, Glusman G, Kasper D, Madan A, Rodrigues S, Fahey J, Wessels MR, Rubens CE "Structural and genetic diversity of group B streptococcus capsular polysaccharides" -
Infection and Immunity 73(5) (2005) 3096-3103
Group B Streptococcus (GBS) is an important pathogen of neonates, pregnant women, and immunocompromised individuals. GBS isolates associated with human infection produce one of nine antigenically distinct capsular polysaccharides which are thought to play a key role in virulence. A comparison of GBS polysaccharide structures of all nine known GBS serotypes together with the predicted amino acid sequences of the proteins that direct their synthesis suggests that the evolution of serotype-specific capsular polysaccharides has proceeded through en bloc replacement of individual glycosyltransferase genes with DNA sequences that encode enzymes with new linkage specificities. We found striking heterogeneity in amino acid sequences of synthetic enzymes with very similar functions, an observation that supports horizontal gene transfer rather than stepwise mutagenesis as a mechanism for capsule variation. Eight of the nine serotypes appear to be closely related both structurally and genetically, whereas serotype VIII is more distantly related. This similarity in polysaccharide structure strongly suggests that the evolutionary pressure toward antigenic variation exerted by acquired immunity is counterbalanced by a survival advantage conferred by conserved structural motifs of the GBS polysaccharides
Bacterial Proteins, Streptococcus agalactiae, Bacterial Capsules, Genetic Variation
NCBI PubMed ID: 15845517Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: craig.rubens@seattlechildrens.org
Institutions: Division of Infectious Diseases, Children's Hospital, University of Washington, Seattle, WA 98109, USA, Channing Division of Infectious Diseases, Children's Hospital Boston, Department of Microbiology and Molecular Genetics, Harvard Medical School Boston, Massachusetts, Institute for Systems Biology and Division of Infectious Diseases, Children's Hospital, University of Washington, 3 Seattle, Washington
Methods: genetic methods, biosynthetic methods
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Next 15 structure(s)
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