Found 9 structures.
Displayed structures from 1 to 9
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 2847
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ P-7)-+
| |
a-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 linear B blood-group determinant
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_241108,IEDB_918314,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
Expand this compound
Collapse this compound
2. Compound ID: 2867
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-+ | P-7)-+
| | |
a-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-D-gro-a-D-manHepp-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 linear B blood-group determinant
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_241108,IEDB_918314,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1006
Monteiro MA, Appelmelk BJ, Rasko DA, Moran AP, Hynes SO, MacLean LL, Chan KH, Michael FS, Logan SM, O'Rourke J, Lee A, Taylor DE, Perry MB "Lipopolysaccharide structures of Helicobacter pylori genomic strains 26695 and J99, mouse model H. pylori Sydney strain, H. pylori P466 carrying sialyl Lewis X, and H. pylori UA915 expressing Lewis B. Classification of H. pylori lipopolysaccharides into glycotype families" -
European Journal of Biochemistry 267(2) (2000) 305-320
This study describes the molecular makeup of the cell-wall lipopolysaccharides (LPSs) (O-chain polysaccharide→core oligosaccharide→lipid A) from five Helicobacter pylori strains: H. pylori 26695 and J99, the complete genome sequences of which have been published, the established mouse model Sydney strain (SS1), and the symptomatic strains P466 and UA915. All chemical and serological experiments were performed on the intact LPSs. H. pylori 26695 and SS1 possessed either a low-Mr semi-rough-form LPS carrying mostly a single Ley type-2 blood-group determinant in the O-chain region covalently attached to the core oligosaccharide or a high-Mr smooth-form LPS, as did strain J99, with an elongated partially fucosylated type-2 N-acetyllactosamine (polyLacNAc) O-chain polymer, terminated mainly by a Lex blood-group determinant, connected to the core oligosaccharide. In the midst of semi-rough-form LPS glycoforms, H. pylori 26695 and SS1 also expressed in the O-chain region a difucosylated antigen, α-L-Fucp(1-3)-α-L-Fucp(1-4)-β-D-GlcpNAc, and the cancer-cell-related type-1 or type-2 linear B-blood-group antigen, α-D-Galp(1-3)-β-D-Galp(1-3 or 4)-β-D-GlcpNAc. The LPS of H. pylori strain P466 carried the cancer-associated type-2 sialyl Lex blood-group antigen, and the LPS from strain UA915 expressed a type-1 Leb blood-group unit. These findings should aid investigations that focus on identifying and characterizing genes responsible for LPS biosynthesis in genomic strains 26695 and J99, and in understanding the role of H. pylori LPS in animal model studies. The LPSs from the H. pylori strains studied to date were grouped into specific glycotype families.
Lipopolysaccharide, structure, Helicobacter pylori, Lewis x, histo-blood groups, glycotypes
NCBI PubMed ID: 10632700Publication DOI: 10.1046/j.1432-1327.2000.01007.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
Methods: FAB-MS, NMR
Expand this compound
Collapse this compound
3. Compound ID: 2876
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| |
a-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 linear B blood-group determinant
Contained glycoepitopes: IEDB_115013,IEDB_120354,IEDB_123890,IEDB_130645,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_241108,IEDB_918314,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1006
Monteiro MA, Appelmelk BJ, Rasko DA, Moran AP, Hynes SO, MacLean LL, Chan KH, Michael FS, Logan SM, O'Rourke J, Lee A, Taylor DE, Perry MB "Lipopolysaccharide structures of Helicobacter pylori genomic strains 26695 and J99, mouse model H. pylori Sydney strain, H. pylori P466 carrying sialyl Lewis X, and H. pylori UA915 expressing Lewis B. Classification of H. pylori lipopolysaccharides into glycotype families" -
European Journal of Biochemistry 267(2) (2000) 305-320
This study describes the molecular makeup of the cell-wall lipopolysaccharides (LPSs) (O-chain polysaccharide→core oligosaccharide→lipid A) from five Helicobacter pylori strains: H. pylori 26695 and J99, the complete genome sequences of which have been published, the established mouse model Sydney strain (SS1), and the symptomatic strains P466 and UA915. All chemical and serological experiments were performed on the intact LPSs. H. pylori 26695 and SS1 possessed either a low-Mr semi-rough-form LPS carrying mostly a single Ley type-2 blood-group determinant in the O-chain region covalently attached to the core oligosaccharide or a high-Mr smooth-form LPS, as did strain J99, with an elongated partially fucosylated type-2 N-acetyllactosamine (polyLacNAc) O-chain polymer, terminated mainly by a Lex blood-group determinant, connected to the core oligosaccharide. In the midst of semi-rough-form LPS glycoforms, H. pylori 26695 and SS1 also expressed in the O-chain region a difucosylated antigen, α-L-Fucp(1-3)-α-L-Fucp(1-4)-β-D-GlcpNAc, and the cancer-cell-related type-1 or type-2 linear B-blood-group antigen, α-D-Galp(1-3)-β-D-Galp(1-3 or 4)-β-D-GlcpNAc. The LPS of H. pylori strain P466 carried the cancer-associated type-2 sialyl Lex blood-group antigen, and the LPS from strain UA915 expressed a type-1 Leb blood-group unit. These findings should aid investigations that focus on identifying and characterizing genes responsible for LPS biosynthesis in genomic strains 26695 and J99, and in understanding the role of H. pylori LPS in animal model studies. The LPSs from the H. pylori strains studied to date were grouped into specific glycotype families.
Lipopolysaccharide, structure, Helicobacter pylori, Lewis x, histo-blood groups, glycotypes
NCBI PubMed ID: 10632700Publication DOI: 10.1046/j.1432-1327.2000.01007.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
Methods: FAB-MS, NMR
Expand this compound
Collapse this compound
4. Compound ID: 3452
|
-4)-b-D-Quip3NAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: microbial carbohydrate determinants
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_241108,IEDB_918314,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1308
Zatonsky GV, Bystrova OV, Kocharova NA, Shashkov AS, Knirel YA, Kholodkova EV, Stanislavsky ES "Structure of a neutral O-specific polysaccharide of the bacterium Providencia alcalifaciens O5" -
Biochemistry (Moscow) 64(5) (1999) 523-527
A neutral polysaccharide containing D-galactose, 2-acetamido-2-deoxy-D-glucose, and 3-acetamido-3,6-dideoxy-D-glucose (Qui3NAc) in the ratios 2:1:1 was obtained by mild acid degradation of lipopolysaccharide of the bacterium Providencia alcalifaciens O5 followed by gel chromatography and ion-exchange chromatography or treatment with anhydrous hydrogen fluoride. On the basis of full acid hydrolysis, methylation, and 1H- and 13C NMR spectroscopy, including two-dimensional correlation spectroscopy (COSY), total correlation spectroscopy (TOCSY), H-detected heteronuclear 1H,13C single-quantum coherence (HSQC), and nuclear Overhauser effect spectroscopy (NOESY), the following structure of the linear tetrasaccharide repeating unit of the polysaccharide was established:
Lipopolysaccharide, LPS, structure, polysaccharide, O-antigen, antibodies, epitope, monoclonal, monoclonal antibody, bacteria, neutral, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, translation, 3-Acetamido-3, 6-dideoxy-d-glucose
NCBI PubMed ID: 10381612Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Mechnikov Central Research Institute for Vaccines and Sera, Ministry of Public Health of russia, 103064 Moscow, Russia
Methods: NMR-2D, methylation, NMR
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4362
Ovchinnikova OG, Liu B, Guo D, Kocharova NA, Bialczak-Kokot M, Shashkov AS, Feng L, Rozalski A, Wang L, Knirel YA "Structural, serological, and genetic characterization of the O-antigen of Providencia alcalifaciens O40" -
FEMS Immunology and Medical Microbiology 66(3) (2012) 382-392
The O-polysaccharide chain of the lipopolysaccharide (O-antigen) on the bacterial cell surface is one of the most structurally variable cell components and serves as a basis for serotyping of Gram-negative bacteria, including human opportunistic pathogens of the genus Providencia. In this work, the O-antigen of Providencia alcalifaciens O40 was obtained by mild acid degradation of the isolated lipopolysaccharide and studied by chemical methods and high-resolution NMR spectroscopy. The following structure of the O-polysaccharide was established: -4)-b-D-Quip3NFo-(1-3)-a-D-Galp-(1-3)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1- where GlcA stands for glucuronic acid and Qui3NFo for 3,6-dideoxy-3-formamidoglucose. The O40-antigen was found to be structurally and serologically related to the O-antigens of P. alcalifaciens O5 and Providencia stuartii O18. The O40-antigen gene cluster between cpxA and yibK was sequenced, and the gene functions were predicted in silico. In agreement with the O-polysaccharide structure established, the genes for the synthesis of dTDP-D-Qui3NFo, UDP-D-Gal, UDP-D-GlcA, and UDP-D-GalNAc as well as those encoding three glycosyltransferases, flippase (Wzx), and O-antigen polymerase (Wzy) were recognized. In addition, homologues of wza, wzb, and wzc genes, which are required for the surface expression of capsular polysaccharides, were found within the gene cluster, suggesting that the O-polysaccharide studied is a part of the capsule-related form of the lipopolysaccharide called K(LPS).
Lipopolysaccharide, Providencia, Providencia alcalifaciens, 3, O-antigen gene cluster, O-Polysaccharide structure, 6-dideoxy-3-formamidoglucose
NCBI PubMed ID: 23163869Publication DOI: 10.1111/1574-695X.12002Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: olga.ovchinnikova@gmail.com
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, ESI-MS, mild acid hydrolysis, serological methods
- 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
- 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
Expand this compound
Collapse this compound
5. Compound ID: 7995
Structure type: oligomer
Trivial name: oligosaccharide type 1 chains of antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140125,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149558,IEDB_150899,IEDB_150948,IEDB_151528,IEDB_151531,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_156570,IEDB_157006,IEDB_174030,IEDB_174333,IEDB_190606,IEDB_241108,IEDB_461709,IEDB_461719,IEDB_461722,IEDB_918314,SB_100,SB_137,SB_148,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 3520
Moran AP "Relevance of fucosylation and Lewis antigen expression in the bacterial gastroduodenal pathogen Helicobacter pylori" -
Carbohydrate Research 343(12) (2008) 1952-1965
Helicobacter pylori is a prevalent bacterial, gastroduodenal pathogen of humans that can express Lewis (Le) and related antigens in the O-chains of its surface lipopolysaccharide. The O-chains of H. pylori are commonly composed of internal Le(x) units with terminal Le(x) or Le(y) units or, in some strains, with additional units of Le(a), Le(b), Le(c), sialyl-Le(x) and H-1 antigens, as well as blood groups A and B, thereby producing a mosaicism of antigenic units expressed. The genetic determination of the Le antigen biosynthetic pathways in H. pylori has been studied, and despite striking functional similarity, low sequence homology occurs between the bacterial and mammalian α(1,3/4)- and α(1,2)-fucosyltransferases. Factors affecting Le antigen expression in H. pylori, that can influence the biological impact of this molecular mimicry, include regulation of fucosyltransferase genes through slipped-strand mispairing, the activity and expression levels of the functional enzymes, the preferences of the expressed enzyme for distinctive acceptor molecules and the availability of activated sugar intermediates. Le mimicry was initially implicated in immune evasion and gastric adaptation by the bacterium, but more recent studies show a role in gastric colonization and bacterial adhesion with galectin-3 identified as the gastric receptor for polymeric Le(x) on the bacterium. From the host defence aspect, innate immune recognition of H. pylori by surfactant protein D is influenced by the extent of LPS fucosylation. Furthermore, Le antigen expression affects both the inflammatory response and T-cell polarization that develops after infection. Although controversial, evidence suggests that long-term H. pylori infection can induce autoreactive anti-Le antibodies cross-reacting with the gastric mucosa, in part leading to the development of gastric atrophy. Thus, Le antigen expression and fucosylation in H. pylori have multiple biological effects on pathogenesis and disease outcome.
molecular mimicry, Helicobacter pylori, Fucosyltransferases, bacterial pathogenesis, Lewis antigens, fucosylation
NCBI PubMed ID: 18279843Publication DOI: 10.1016/j.carres.2007.12.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: anthony.moran@nuigalway.ie
Institutions: Department of Microbiology, School of Natural Sciences, National University of Ireland, Galway, Ireland, Institute for Glycomics, Gold Coast Campus, Griffith University, Queensland 4222, Australia
Methods: NMR, sugar analysis, MS, genetic methods
Expand this compound
Collapse this compound
6. Compound ID: 9095
Structure type: oligomer
Trivial name: oligosaccharide type 1 chains of B-1 antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140125,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149558,IEDB_150899,IEDB_150948,IEDB_151528,IEDB_151531,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_156570,IEDB_157006,IEDB_174030,IEDB_174333,IEDB_190606,IEDB_241108,IEDB_461709,IEDB_461719,IEDB_461722,IEDB_918314,SB_100,SB_137,SB_148,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 3903
Moran A "The Role of Endotoxin in Infection: Helicobacter pylori and Campylobacter jejuni" -
Book: Endotoxins: Structure, Function and Recognition (series: Subcellular Biochemistry, Part 1) (2010) Vol. 53, Chapter 10, 209-240
Both Helicobacter pylori and Campylobacter jejuni are highly prevalent Gram-negative microaerophilic bacteria which are gastrointestinal pathogens of humans; H. pylori colonizes the gastroduodenal compartment and C. jejuni the intestinal mucosa. Although H. pylori causes chronic gastric infection leading to gastritis, peptic ulcers and eventually gastric cancer while C. jejuni causes acute infection inducing diarrhoeal disease, the endotoxin molecules of both bacterial species contrastingly contribute to their pathogenesis and the autoimmune sequelae each induces. Compared with enterobacterial endotoxin, that of H. pylori has significantly lower endotoxic and immuno-activities, the molecular basis for which is the underphosphorylation and underacylation of the lipid A component that interacts with immune receptors. This induction of low immunological responsiveness by endotoxin may aid the prolongation of H. pylori infection and therefore infection chronicity. On the other hand, this contrasts with acute infection-causing C. jejuni where overt inflammation contributes to pathology and diarrhoea production, and whose endotoxin is immunologically and endotoxically active. Futhermore, both H. pylori and C. jejuni exhibit molecular mimicry in the saccharide components of their endotoxins which can induce autoreactive antibodies; H. pylori expresses mimicry of Lewis and some ABO blood group antigens, C. jejuni mimicry of gangliosides. The former has been implicated in influencing the development of inflammation and gastric atrophy (a precursor of gastic cancer), the latter is central to the development of the neurological disorder Guillain-Barre syndrome. Both diseases raise important questions concerning infection-induced autoimmunity awaiting to be addressed.
lipid A, Campylobacter jejuni, molecular mimicry, Helicobacter pylori, bacterial pathogenesis
NCBI PubMed ID: 20593269Publication DOI: 10.1007/978-90-481-9078-2_10Publisher: Springer Science+Business Media B.V.
Correspondence: anthony.moran@nuigalway.ie
Editors: Wang X, Quinn PJ
Institutions: Laboratory of Molecular Biochemistry, Microbiology, School of Natural Sciences, National University of Ireland, Galway, Ireland
Expand this compound
Collapse this compound
7. Compound ID: 9994
|
L-Rhap-(1-2)-L-Rhap-(1-6)-+
|
-3)-L-Rhap-(1-3)-D-Galp-(1-3)-D-Galp-(1-3)-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_133754,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_225177,IEDB_241108,IEDB_742246,IEDB_885823,IEDB_918313,IEDB_918314,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4167
Takeuchi M, Yokota A, Misaki A "Comparative structures of the cell-wall polysaccharides of four species of the genus Microbacterium" -
Journal of General and Applied Microbiology 36 (1990) 255-271
Cell-wall polysaccharides purified from four species of the genus Microbacterium were characterized in relation to their taxonomy, based on 1H-NMR and 13C-NMR spectrometry, methylation analysis and Smith degradation. The polysaccharide isolated from M. imperiale IFO 12610 contained a backbone consisting of heptasaccharide repeating-units, to which side chains of L-rhamnopyranosyl-(1→2)-D-mannopyranosyl-(1→2)-D-mannopyranoses as branches were attached to position 6 of the 3-linked D-galactopyranose residues. The polysaccharide of M. lacticum IFO 14135 contained hexasaccharide repeating-units, to which disaccharide groups of L-rhamnopyranosyl-(1→2)-L-rhamnopyranoses were attached to position 6 of the 3-linked D-galactopyranose residues to form branches. The polysaccharide of M. arborescens IFO 3750 consists of pentasaccharide repeating-units, and single D-mannopyranosyl groups were attached as branches to position 6 of the 3-linked D-galactofuranose residues. The polysaccharide of M. laevaniformans IFO 14471 had a more complicated structure consisting of decasaccharide repeating-units, and branches occur at three different positions. Thus, the cell-wall polysaccharides of the former three species were similar in their basic structures, but that of M. laevaniformans has a significantly different structure. These results indicated that the structures of cell-wall polysaccharides are heterogeneous in the genus Microbacterium and may characterize the species in the genus.
Journal NLM ID: 0165543Publisher: Tokyo: Microbiology Research Foundation
Institutions: Institute for Fermentation, Osaka, Japan, Faculty of Science of Living, Osaka City University, Osaka, Japan
Methods: gel filtration, 13C NMR, 1H NMR, methylation, IR, GLC-MS, partial acid hydrolysis, Smith degradation, HPLC
Expand this compound
Collapse this compound
8. Compound ID: 10686
|
a-Colp-(1-4)-+
|
a-Colp-(1-2)-+ |
| |
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-Galp?Ac-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_225177,IEDB_241108,IEDB_885823,IEDB_918314,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_36,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4358
Nazarenko EL, Crawford RJ, Ivanova EP "The structural diversity of carbohydrate antigens of selected Gram-negative marine bacteria" -
Marine Drugs 9(10) (2011) 1914-1954
Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobacteria phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.
O-specific polysaccharides, carbohydrate antigens, marine microorganisms
NCBI PubMed ID: 22073003Publication DOI: 10.3390/md9101914Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: elnaz@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia, Faculty of Life and Social Sciences, Swinburne University of Technology, PO Box 218, Hawthorn, Victoria 3122, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, mild acid hydrolysis, HPAEC, ESI-FTICR-MS, Smith degradation, chemical methods, MALDI-TOF MS, MS, de-O-acetylation, NMR-1D, GPC, alkaline hydrolysis, periodate oxidation, CE-ESI-MS, CE-MS, hydrazinolysis
Expand this compound
Collapse this compound
9. Compound ID: 10688
|
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-Galp?Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149558,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_156570,IEDB_190606,IEDB_225177,IEDB_241108,IEDB_885823,IEDB_918314,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_36,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4358
Nazarenko EL, Crawford RJ, Ivanova EP "The structural diversity of carbohydrate antigens of selected Gram-negative marine bacteria" -
Marine Drugs 9(10) (2011) 1914-1954
Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobacteria phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.
O-specific polysaccharides, carbohydrate antigens, marine microorganisms
NCBI PubMed ID: 22073003Publication DOI: 10.3390/md9101914Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: elnaz@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia, Faculty of Life and Social Sciences, Swinburne University of Technology, PO Box 218, Hawthorn, Victoria 3122, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, mild acid hydrolysis, HPAEC, ESI-FTICR-MS, Smith degradation, chemical methods, MALDI-TOF MS, MS, de-O-acetylation, NMR-1D, GPC, alkaline hydrolysis, periodate oxidation, CE-ESI-MS, CE-MS, hydrazinolysis
Expand this compound
Collapse this compound
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (record IDs):
Execution: 2 sec