Found 15 structures.
Displayed structures from 1 to 15
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 1236
|
a-Colp-(1-2)-b-Yerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
Yer = 3,6-dideoxy-4-C-[(S)-1-hydroxyethyl]-D-xylo-hexose (yersiniose A) |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 380
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- Article ID: 4005
Cunneen MM, Pacinelli E, Song WC, Reeves PR "Genetic analysis of the O-antigen gene clusters of Yersinia pseudotuberculosis O:6 and O:7" -
Glycobiology 21(9) (2011) 1140-1146
Among the 21 O-polysaccharide (OPS) O-antigen based serotypes described for Yersinia pseudotuberculosis, those of O:6 and O:7 are unusual in that both contain colitose (4-keto-3,6 dideoxy-D-mannose or 4-keto-3,6-dideoxy-L-xylo-hexose), which has not otherwise been reported for this species, and the O:6 OPS also contains yersiniose A (4-C[(R)-1-hydroxyethyl]-3,6,dideoxy-D-xylo-hexose), another unusual dideoxyhexose sugar. In Y. pseudotuberculosis the genes for OPS synthesis generally cluster together between the hemH and gsk loci. Here we present the sequences of the OPS gene clusters of Y. pseudotuberculosis O:6 and O:7, and the location of the genes required for synthesis of these OPSs, except that there is still ambiguity regarding allocation of some of the glycosyltransferase functions. The O:6 and O:7 gene clusters have much in common with each other, but differ substantially from the group of 13 gene clusters already sequenced, which share several features and sequence similarities. We also present a possible sequence of events for the derivation of the O:6 and O:7 gene clusters from the most closely related of the set of 13 sequenced previously.
Yersinia pseudotuberculosis, O-antigen gene cluster
NCBI PubMed ID: 21325338Publication DOI: 10.1093/glycob/cwr010Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia
Methods: genetic methods
- Article ID: 4044
Kenyon JJ, De Castro C, Cunneen MM, Reeves PR, Molinaro A, Holst O, Skurnik M "The genetics and structure of the O-specific polysaccharide of Yersinia pseudotuberculosis serotype O:10 and its relationship to Escherichia coli O111 and Salmonella enterica O35" -
Glycobiology 21(9) (2011) 1131-1139
The O-specific polysaccharide (OPS) is a variable constituent of the lipopolysaccharide of Gram-negative bacteria. The polymorphic nature of OPSs within a species is usually first defined serologically, and the current serotyping scheme for Yersinia pseudotuberculosis consists of 21 O serotypes of which 15 have been characterized genetically and structurally. Here, we present the structure and DNA sequence of Y. pseudotuberculosis O:10 OPS. The O unit consists of one residue each of d-galactopyranose, N-acetyl-d-galactosamine (2-amino-2-deoxy-d-galactopyranose) and d-glucopyranose in the backbone, with two colitose (3,6-dideoxy-l-xylo-hexopyranose) side-branch residues. This structure is very similar to that shared by Escherichia coli O111 and Salmonella enterica O35. The gene cluster sequences of these serotypes, however, have only low levels of similarity to that of Y. pseudotuberculosis O:10, although there is significant conservation of gene order. Within Y. pseudotuberculosis, the O10 structure is most closely related to the O:6 and O:7 structures.
O-specific polysaccharide, colitose, Yersinia pseudotuberculosis O:10, Escherichia coli O111, Salmonella enterica O35
NCBI PubMed ID: 21321053Publication DOI: 10.1093/glycob/cwr006Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: P.R. Reeves
; C. De Castro
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia.
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, mild acid hydrolysis
- 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: 5010
Kenyon JJ, Cunneen MM, Reeves PR "Genetics and evolution of Yersinia pseudotuberculosis O-specific polysaccharides: a novel pattern of O-antigen diversity" -
FEMS Microbiology Reviews 41(2) (2017) 200-217
O-antigen polysaccharide is a major immunogenic feature of the lipopolysaccharide of Gram-negative bacteria, and most species produce a large variety of forms that differ substantially from one another. There are 18 known O-antigen forms in the Yersinia pseudotuberculosis complex, which are typical in being composed of multiple copies of a short oligosaccharide called an O unit. The O-antigen gene clusters are located between the hemH and gsk genes, and are atypical as 15 of them are closely related, each having one of five downstream gene modules for alternative main-chain synthesis, and one of seven upstream modules for alternative side-branch sugar synthesis. As a result, many of the genes are in more than one gene cluster. The gene order in each module is such that, in general, the earlier a gene product functions in O-unit synthesis, the closer the gene is to the 5 end for side-branch modules or the 3 end for main-chain modules. We propose a model whereby natural selection could generate the observed pattern in gene order, a pattern that has also been observed in other species.
Lipopolysaccharide, serotype, O antigen, gene cluster, O-specific polysaccharide, Yersinia pseudotuberculosis, O-antigen polysaccharide
NCBI PubMed ID: 28364730Publication DOI: 10.1093/femsre/fux002Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW 2006, Australia, Institute of Health and Biomedical Innovation, Queensland University of Technology. Brisbane, QLD 4001, Australia
Methods: function analysis of gene clusters
- Article ID: 6089
Knirel YA, Anisimov AP, Kislichkina AA, Kondakova AN, Bystrova OV, Vagaiskaya AS, Shatalin KY, Shashkov AS, Dentovskaya SV "Lipopolysaccharide of the Yersinia pseudotuberculosis Complex" -
Biomolecules 11(10) (2021) 1410
Lipopolysaccharide (LPS), localized in the outer leaflet of the outer membrane, serves as the major surface component of the Gram-negative bacterial cell envelope responsible for the activation of the host's innate immune system. Variations of the LPS structure utilized by Gram-negative bacteria promote survival by providing resistance to components of the innate immune system and preventing recognition by TLR4. This review summarizes studies of the biosynthesis of Yersinia pseudotuberculosis complex LPSs, and the roles of their structural components in molecular mechanisms of yersiniae pathogenesis and immunogenesis.
core, Pathogenesis, lipid A, Yersinia pseudotuberculosis, lipopolysaccharide (LPS), Yersinia pestis, Plague, pathogenicity factor
NCBI PubMed ID: 34680043Publication DOI: 10.3390/biom11101410Journal NLM ID: 101596414Publisher: Basel, Switzerland: MDPI
Correspondence: Y.A. Knirel
; S.V. Dentovskaya
Institutions: Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory for Plague Microbiology, Especially Dangerous Infections Department, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Russia, Department of Biochemistry and Molecular Pharmacology, New York University School of Medicine, New York, NY 10016, USA
Expand this compound
Collapse this compound
2. Compound ID: 2511
|
R-Lac-(2-3)-a-D-Glcp-(1-3)-+
|
-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-b-D-Ribf-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_151531,IEDB_158539,IEDB_225177,IEDB_423141,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 854
Knirel YA, Kaca W, Paramonov NA, Cedzynski M, Vinogradov EV, Ziolkowski A, Shashkov AS, Rozalski A "Structure of the O-specific polysaccharide of Proteus vulgaris O25 containing 3-O-[(R)-1-carboxyethyl]-D-glucose" -
European Journal of Biochemistry 247 (1997) 951-954
The O-specific polysaccharide of Proteus vulgaris O25 was studied by acid hydrolysis and by 1H NMR and 13C NMR spectroscopies, including one-dimensional NOE and two-dimensional COSY and heteronuclear 13C,1H correlation (HETCOR) spectroscopy. The polysaccharide was found to contain 3-O-[(R)-1-carboxyethyl]-D-glucose (D-RGlc), and the following structure of the pentasaccharide repeating unit was established: [structure in text]
Lipopolysaccharide, LPS, structure, polysaccharide, identification, acid, O-specific, O-specific polysaccharide, Proteus, Proteus vulgaris, isomer, D-glucose, glycolactilic acid
NCBI PubMed ID: 9288919Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, acid hydrolysis, optical rotation measurement
- Article ID: 1466
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 3434
Arabski M, Graboski S, Konieczna I, Kaca W, Kondakova AN, Perepelov AV, Senchenkova SN, Shashkov AS, Knirel YA "Serotyping of clinical isolates belonging to Proteus mirabilis serogroup O36 and structural elucidation of the O36-antigen polysaccharide" -
FEMS Immunology and Medical Microbiology 53(3) (2008) 395-403
The O-specific polysaccharide (OPS) isolated from the lipopolysaccharide of Proteus mirabilis O36 was found to have a pentasaccharide repeating unit of the following structure: →2)-β-D-Ribf-(1→4)-β-D-Galp-(1→4)-α-D-GlcpNAc6Ac-(1→4)-β-D-Galp-(1→3)-α-D-GlcpNAc-(1→. The structure is unique among Proteus OPS, which is in agreement with the classification of this strain into a separate Proteus O-serogroup. Remarkably, the P. mirabilis O36-polysaccharide has the same structure as the OPS of Escherichia coli O153, except that the latter is devoid of O-acetyl groups. The cross-reaction of anti-O36 antibodies with the O-part of E. coli O153 lipopolysaccharide is observed. In the present study, two steps of serotyping Proteus strains are proposed: screening of dry mass with enzyme-linked immunosorbent assay and immunoblot with the crude lipopolysaccharides. This method allowed serotyping of 99 P. mirabilis strains infecting the human urinary tract. Three strains were classified into serogroup O36. The migration pattern of these lipopolysaccharides fraction with long O-specific PSs was similar to the standard laboratory P. mirabilis O36 (Prk 62/57) lipopolysaccharide. The relatively low number of clinical strains belonging to serogroup O36 did not correspond to the presence of anti-P. mirabilis O36 antibodies in the blood donors' sera. Twenty-five percent of tested sera contained a statistically significant elevated level of antibodies reacting with thermostable surface antigens of P. mirabilis O36. The presence and amount of antibodies correlated with Thr399Ile TLR4 polymorphism types (P=0.044).
Escherichia coli, O-specific polysaccharide, Proteus mirabilis, serological classification, bacterial polysaccharide structure, TLR4
NCBI PubMed ID: 18625011Publication DOI: 10.1111/j.1574-695X.2008.00440.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: arabski@pu.kielce.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Microbiology, Institute of Biology, Świętokrzyska Academy, ul. Świę tokrzyska 15,25-406, Kielce, Poland, Department of General Microbiology, Institute of Microbiology and Immunology, University of Łódź, Banacha, Łódź, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, GLC, serological methods, genetic methods
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
Expand this compound
Collapse this compound
3. Compound ID: 4158
|
R-Lac-(2-3)-a-D-Glcp-(1-3)-+
|
-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-b-D-Ribf-(1-
Lac = 1-carboxyethyl |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_151531,IEDB_158539,IEDB_225177,IEDB_423141,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1533
Kondakova AN, Fudala R, Senchenkova SN, Shashkov AS, Knirel YA, Kaca W "Structure of a lactic acid ether-containing and glycerol phosphate-containing O-polysaccharide from Proteus mirabilis O40" -
Carbohydrate Research 340(9) (2005) 1612-1617
An O-polysaccharide was isolated by mild acid hydrolysis from the lipopolysaccharide of Proteus mirabilis O40 and studied by NMR spectroscopy, including 2D 1H, 1H COSY, TOCSY, ROESY, and 1H, 13C HMQC experiments, along with chemical methods. The polysaccharide was found to contain an ether of GlcNAc with lactic acid and glycerol phosphate in the main chain and to have the following structure: →3)-β-D-GlcpNAc4(R-Lac)-(1→3)-α-D-Galp-(1→3)-D-Gro-1-P-(O→3)-β-D-GlcpNAc-(1→ where D-GlcpNAc4(R-Lac) stands for 2-acetamido-4-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucose. This structure is unique among the known structures of the Proteus O-polysaccharides, which is in agreement with the classification of the strain studied into a separate O-serogroup. A serological relatedness of P. mirabilis O40 with some other Proteus strains was revealed and discussed in view of the O-polysaccharide structures.
Lipopolysaccharide, lipopolysaccharides, oligosaccharide, structure, blood, human, O-antigen, repeating unit, O antigen, acid, O-polysaccharide, O polysaccharide, neutral, Proteus, Proteus mirabilis, biological, activity, biological activity, preparation, serum, glycerol, influence, lactic acid, protease
NCBI PubMed ID: 15890320Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland, Institute of Biology, Swietokrzyska Academy, 25-406 Kielce, Poland
Methods: NMR, composition analysis
Expand this compound
Collapse this compound
4. Compound ID: 4187
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,IEDB_423141,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1554
Perry MB, MacLean LL, Vinogradov E "Structural characterization of the antigenic capsular polysaccharide and lipopolysaccharide O-chain produced by Actinobacillus pleuropneumoniae serotype 15" -
Biochemistry and Cell Biology 83(1) (2005) 61-69
The specific capsular polysaccharide produced by Actinobacillus pleuropneumoniae serotype 15 was determined to be a high-molecular-mass polymer having [alpha]D + 69 degrees (water) and composed of a linear backbone of phosphate diester linked disaccharide units of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc) and 2-acetamido-2-deoxy-D-galactose (D-GalNAc) residues (1:1). Thirty percent of the D-GalNAc residues were substituted at O-4 by beta-D-galactopyranose (beta-D-Galp) residues. Through the application of chemical and NMR methods, the capsule, which defines the serotype specificity of the bacterium, was found to have the structure [structure: see text]. The O-polysaccharide (O-PS) component of the A. pleuropneumoniae serotype 15 lipopolysaccharide (LPS) was characterized as a linear unbranched polymer of repeating pentasaccharide units composed of D-glucose (2 parts) and D-galactose (3 parts), shown to have the structure [structure: see text]. The O-PS was chemically identical with the O-antigen previously identified in the LPSs produced by A. pleuropneumoniae serotypes 3 and 8.
Lipopolysaccharide, capsule, 2-acetamido-2-deoxy-D-galactose, Actinobacillus pleuropneumoniae, 2-acetamido-2-deoxy-D-glucose, Actinobacillus pleuropneumoniae serotype 15
NCBI PubMed ID: 15746967Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, ON K1A 0R6, Canada
Methods: methylation, NMR, dephosphorylation, deamination, periodate oxidation
Expand this compound
Collapse this compound
5. Compound ID: 4188
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_151531,IEDB_423141
The structure is contained in the following publication(s):
- Article ID: 1554
Perry MB, MacLean LL, Vinogradov E "Structural characterization of the antigenic capsular polysaccharide and lipopolysaccharide O-chain produced by Actinobacillus pleuropneumoniae serotype 15" -
Biochemistry and Cell Biology 83(1) (2005) 61-69
The specific capsular polysaccharide produced by Actinobacillus pleuropneumoniae serotype 15 was determined to be a high-molecular-mass polymer having [alpha]D + 69 degrees (water) and composed of a linear backbone of phosphate diester linked disaccharide units of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc) and 2-acetamido-2-deoxy-D-galactose (D-GalNAc) residues (1:1). Thirty percent of the D-GalNAc residues were substituted at O-4 by beta-D-galactopyranose (beta-D-Galp) residues. Through the application of chemical and NMR methods, the capsule, which defines the serotype specificity of the bacterium, was found to have the structure [structure: see text]. The O-polysaccharide (O-PS) component of the A. pleuropneumoniae serotype 15 lipopolysaccharide (LPS) was characterized as a linear unbranched polymer of repeating pentasaccharide units composed of D-glucose (2 parts) and D-galactose (3 parts), shown to have the structure [structure: see text]. The O-PS was chemically identical with the O-antigen previously identified in the LPSs produced by A. pleuropneumoniae serotypes 3 and 8.
Lipopolysaccharide, capsule, 2-acetamido-2-deoxy-D-galactose, Actinobacillus pleuropneumoniae, 2-acetamido-2-deoxy-D-glucose, Actinobacillus pleuropneumoniae serotype 15
NCBI PubMed ID: 15746967Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, ON K1A 0R6, Canada
Methods: methylation, NMR, dephosphorylation, deamination, periodate oxidation
Expand this compound
Collapse this compound
6. Compound ID: 6472
|
a-Colp-(1-2)-b-Yerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
Yer = 3,6-dideoxy-4-C-[(R)-1-hydroxyethyl]-D-xylo-hexose (yersiniose A) |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Expand this compound
Collapse this compound
7. Compound ID: 6476
|
a-Colp-(1-2)-/Variants 0/-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
/Variants 0/ is:
b-iYerp-(1-3)-
OR (exclusively)
b-Yerp-(1-3)- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 2911
Gorshkova RP, Zubkov VA, Isakov VV, Ovodov YS "Structural features of O-specific polysaccharide from lipopolysaccharide of Yersinia pseudotuberculosis VI serovar" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 9 (1983) 1068-1073
Using methylation studies, partial hydrolysis and 13C NMR spectroscopy data, the following structure of O-specific polysaccharide from lipopolysaccharide of Yersinia pseudotuberculosis VI serovar has been proposed: (Formula: see text).
NCBI PubMed ID: 6210095Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Science Centre, Academy of Sciences of the U.S.S.R., Vladivostok
Methods: 13C NMR
Expand this compound
Collapse this compound
8. Compound ID: 6477
|
a-Colp-(1-2)-b-Yerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 2911
Gorshkova RP, Zubkov VA, Isakov VV, Ovodov YS "Structural features of O-specific polysaccharide from lipopolysaccharide of Yersinia pseudotuberculosis VI serovar" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 9 (1983) 1068-1073
Using methylation studies, partial hydrolysis and 13C NMR spectroscopy data, the following structure of O-specific polysaccharide from lipopolysaccharide of Yersinia pseudotuberculosis VI serovar has been proposed: (Formula: see text).
NCBI PubMed ID: 6210095Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Science Centre, Academy of Sciences of the U.S.S.R., Vladivostok
Methods: 13C NMR
Expand this compound
Collapse this compound
9. Compound ID: 8283
|
a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-+
|
b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-4)-a-D-Glcp-(1-2)-a-D-Glcp-(1--/inner core-lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: inner core-lipid A
Trivial name: outer core region
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_141501,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_232584,IEDB_423141,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3622
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. II. The structure of the core region" -
Biochemistry (Moscow) 58(2) (1993) 84-99
This review summarizes data on the structure of the core of bacterial lipopolysaccharides (LPS), an oligosaccharide which binds the lipid moiety of LPS to the O-antigenic polysaccharide chain. Both S-strains with complete LPS and R-mutants having various defects of core biosynthesis are considered. The role of the core in the functioning of the outer membrane and in the manifestation of antigenic specificity of LPS is discussed.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, structure, core, bacteria, core region, region, Gram-negative bacteria, gram negative bacteria, Gram-negative, review, outer membrane, bacterial lipopolysaccharide
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)
Expand this compound
Collapse this compound
10. Compound ID: 8284
|
a-D-Gal-(1-6)-b-D-Glcp-(1-4)-+
|
b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-4)-a-D-Glcp-(1-2)-a-D-Glcp-(1--/inner core-lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: inner core-lipid A
Trivial name: outer core region
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141501,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_232584,IEDB_423141,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 3622
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. II. The structure of the core region" -
Biochemistry (Moscow) 58(2) (1993) 84-99
This review summarizes data on the structure of the core of bacterial lipopolysaccharides (LPS), an oligosaccharide which binds the lipid moiety of LPS to the O-antigenic polysaccharide chain. Both S-strains with complete LPS and R-mutants having various defects of core biosynthesis are considered. The role of the core in the functioning of the outer membrane and in the manifestation of antigenic specificity of LPS is discussed.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, structure, core, bacteria, core region, region, Gram-negative bacteria, gram negative bacteria, Gram-negative, review, outer membrane, bacterial lipopolysaccharide
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)
Expand this compound
Collapse this compound
11. Compound ID: 9410
|
a-Colp-(1-2)-b-iYerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
iYer = 3,6-dideoxy-4-C-[(S)-1-hydroxyethyl]-D-xylo-hexose (yersiniose B) |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 4005
Cunneen MM, Pacinelli E, Song WC, Reeves PR "Genetic analysis of the O-antigen gene clusters of Yersinia pseudotuberculosis O:6 and O:7" -
Glycobiology 21(9) (2011) 1140-1146
Among the 21 O-polysaccharide (OPS) O-antigen based serotypes described for Yersinia pseudotuberculosis, those of O:6 and O:7 are unusual in that both contain colitose (4-keto-3,6 dideoxy-D-mannose or 4-keto-3,6-dideoxy-L-xylo-hexose), which has not otherwise been reported for this species, and the O:6 OPS also contains yersiniose A (4-C[(R)-1-hydroxyethyl]-3,6,dideoxy-D-xylo-hexose), another unusual dideoxyhexose sugar. In Y. pseudotuberculosis the genes for OPS synthesis generally cluster together between the hemH and gsk loci. Here we present the sequences of the OPS gene clusters of Y. pseudotuberculosis O:6 and O:7, and the location of the genes required for synthesis of these OPSs, except that there is still ambiguity regarding allocation of some of the glycosyltransferase functions. The O:6 and O:7 gene clusters have much in common with each other, but differ substantially from the group of 13 gene clusters already sequenced, which share several features and sequence similarities. We also present a possible sequence of events for the derivation of the O:6 and O:7 gene clusters from the most closely related of the set of 13 sequenced previously.
Yersinia pseudotuberculosis, O-antigen gene cluster
NCBI PubMed ID: 21325338Publication DOI: 10.1093/glycob/cwr010Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia
Methods: genetic methods
Expand this compound
Collapse this compound
12. Compound ID: 9527
|
a-Colp-(1-2)-b-iYerp-(1-3)-+
|
-3)-b-D-GlcpNAc-(1-6)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-
iYer = 3,6-dideoxy-4-C-[(R)-1-hydroxyethyl]-D-xylo-hexose (yersiniose B) |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_153207,IEDB_423141,IEDB_423151,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 4044
Kenyon JJ, De Castro C, Cunneen MM, Reeves PR, Molinaro A, Holst O, Skurnik M "The genetics and structure of the O-specific polysaccharide of Yersinia pseudotuberculosis serotype O:10 and its relationship to Escherichia coli O111 and Salmonella enterica O35" -
Glycobiology 21(9) (2011) 1131-1139
The O-specific polysaccharide (OPS) is a variable constituent of the lipopolysaccharide of Gram-negative bacteria. The polymorphic nature of OPSs within a species is usually first defined serologically, and the current serotyping scheme for Yersinia pseudotuberculosis consists of 21 O serotypes of which 15 have been characterized genetically and structurally. Here, we present the structure and DNA sequence of Y. pseudotuberculosis O:10 OPS. The O unit consists of one residue each of d-galactopyranose, N-acetyl-d-galactosamine (2-amino-2-deoxy-d-galactopyranose) and d-glucopyranose in the backbone, with two colitose (3,6-dideoxy-l-xylo-hexopyranose) side-branch residues. This structure is very similar to that shared by Escherichia coli O111 and Salmonella enterica O35. The gene cluster sequences of these serotypes, however, have only low levels of similarity to that of Y. pseudotuberculosis O:10, although there is significant conservation of gene order. Within Y. pseudotuberculosis, the O10 structure is most closely related to the O:6 and O:7 structures.
O-specific polysaccharide, colitose, Yersinia pseudotuberculosis O:10, Escherichia coli O111, Salmonella enterica O35
NCBI PubMed ID: 21321053Publication DOI: 10.1093/glycob/cwr006Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: P.R. Reeves
; C. De Castro
Institutions: Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia.
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, mild acid hydrolysis
Expand this compound
Collapse this compound
13. Compound ID: 9573
|
R-Lac-(2-3)-a-D-Glcp-(1-3)-+
|
-2)-a-L-Rhap-(1-2)-b-D-Ribf-(1-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_151531,IEDB_158539,IEDB_225177,IEDB_423141,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4048
Knirel YA, Perepelov AV, Kondakova AN, Senchenkova SN, Sidorczyk Z, Rozalski A, Kaca W "Structure and serology of O-antigens as the basis for classification of Proteus strains" -
Innate Immunity 17(1) (2011) 70-96
This review is devoted to structural and serological characteristics of the O-antigens (O-polysaccharides) of the lipopolysaccharides of various Proteus species, which provide the basis for classifying Proteus strains to O-serogroups. The antigenic relationships of Proteus strains within and beyond the genus as well as their O-antigen-related bioactivities are also discussed.
Lipopolysaccharide, O-antigen, Proteus, polysaccharide structure, classification, Serological cross-reactivity, immunospecificity
NCBI PubMed ID: 20305038Publication DOI: 10.1177/1753425909360668Journal NLM ID: 101469670Publisher: Sage Publications
Correspondence: yknirel@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, Lodz, Poland, Department of Microbiology, Jan Kochanowski University, Kielce, Poland
- Article ID: 5057
Yu X, Torzewska A, Zhang X, Yin Z, Drzewiecka D, Cao H, Liu B, Knirel YA, Rozalski A, Wang L "Genetic diversity of the O antigens of Proteus species and the development of a suspension array for molecular serotyping" -
PLoS One 12(8) (2017) e0183267
Proteus species are well-known opportunistic pathogens frequently associated with skin wound and urinary tract infections in humans and animals. O antigen diversity is important for bacteria to adapt to different hosts and environments, and has been used to identify serotypes of Proteus isolates. At present, 80 Proteus O-serotypes have been reported. Although the O antigen structures of most Proteus serotypes have been identified, the genetic features of these O antigens have not been well characterized. The O antigen gene clusters of Proteus species are located between the cpxA and secB genes. In this study, we identified 55 O antigen gene clusters of different Proteus serotypes. All clusters contain both the wzx and wzy genes and exhibit a high degree of heterogeneity. Potential functions of O antigen-related genes were proposed based on their similarity to genes in available databases. The O antigen gene clusters and structures were compared, and a number of glycosyltransferases were assigned to glycosidic linkages. In addition, an O serotype-specific suspension array was developed for detecting 31 Proteus serotypes frequently isolated from clinical specimens. To our knowledge, this is the first comprehensive report to describe the genetic features of Proteus O antigens and to develop a molecular technique to identify different Proteus serotypes.
O-antigen, gene cluster, Proteus, glycosyltransferases, serotyping, genomics, genetic diversity, serotype-specific
NCBI PubMed ID: 28817637Publication DOI: 10.1371/journal.pone.0183267Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Lei Wang
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, P. R. China, Tianjin Research Center for Functional Genomics and Biochips, TEDA College, Nankai University, Tianjin, P. R. China, Tianjin Key Laboratory of Microbial Functional Genomics, TEDA College, Nankai University, Tianjin, P. R. China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, TEDA College, Nankai University, Tianjin, P. R. China, Department of Immunobiology of Bacteria, Department of General Microbiology Institute of Microbiology, Biotechnology and Immunology, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland
Methods: PCR, DNA sequencing, genetic methods, function analysis of gene clusters, serotyping
Expand this compound
Collapse this compound
14. Compound ID: 11621
|
-2)-a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_147450,IEDB_150767,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_241096,IEDB_423141,IEDB_461711,IEDB_461719,SB_154,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_7,SB_8,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 4690
Knirel YA, Gabius H, Blixt O, Rapoport EM, Khasbiullina NR, Shilova NV, Bovin NV "Human tandem-repeat-type galectins bind bacterial non-bGal polysaccharides" -
Glycoconjugate Journal 31(1) (2014) 7-12
Galectins are multifunctional effectors, for example acting as regulators of cell growth via protein-glycan interactions. The observation of capacity to kill bacteria for two tandem-repeat-type galectins, which target histo-blood epitopes toward this end (Stowell et al. Nat. Med. 16:295-301, 2010), prompted us to establish an array with bacterial polysaccharides. We addressed the question whether sugar determinants other than ?-galactosides may be docking sites, using human galectins-4, -8, and -9. Positive controls with histo-blood group ABH-epitopes and the E. coli 086 polysaccharide ascertained the suitability of the set-up. Significant signal generation, depending on type of galectin and polysacchride, was obtained. Presence of cognate ?-galactoside-related epitopes within a polysaccharide chain or its branch will not automatically establish binding properties, and structural constellations lacking galactosides, like rhamnan, were found to be active. These data establish the array as valuable screening tool, giving direction to further functional and structural studies.
glycan, Bacterial polysaccharide, ABO, galectin, printed glycan array, rhamnoside
NCBI PubMed ID: 24065176Publication DOI: 10.1007/s10719-013-9497-3Journal NLM ID: 8603310WWW link: doi:10.1007/s10719-013-9497-3Publisher: Kluwer Academic Publishers
Correspondence: bovin@carb.ibch.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, Moscow, Russian Federation, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10
Methods: GPC, mild acid degradation, binding assays
Expand this compound
Collapse this compound
15. Compound ID: 14496
|
R-Lac-(1-3)-a-D-Glcp-(1-3)-+
|
-4)-b-D-GalpNAc-(1-3)-b-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-b-D-Ribf-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_151531,IEDB_158539,IEDB_225177,IEDB_423141,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
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: 3 sec