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: 1341
a-Neup5Ac-(2-3)-+ EtN-(1--P--6)--+
| |
a-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-2)-L-gro-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdo-(2--/lipid A/
|
b-D-Glcp-(1-4)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_153215,IEDB_190606,IEDB_2189047,IEDB_885822,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_37,SB_39,SB_6,SB_68,SB_7,SB_76,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 422
Wood AC, Oldfield NJ, O'Dwyer CA, Ketley JM "Cloning, mutation and distribution of a putative lipopolysaccharide biosynthesis locus in Campylobacter jejuni" -
Microbiology 145(2) (1999) 379-388
A region encoding ORFs with homology to known lipopolysaccharide (LPS) biosynthesis genes was isolated from two strains of Campylobacter jejuni. One of the strains produces LPS, but the second strain is reported to produce only lipooligosaccharide (LOS) and therefore lacks the O-chain. The two strains shared six predicted ORFs, but an additional ORF, orfE, of unknown function was identified in the LOS-producing strain. Mutation of the shared wbeE (rfbE) homologue (orfF) or deletion of five of the seven genes reduced core reactivity with specific antiserum without affecting O-chain production. Mutation of either the capD homologue (orfG) or the unique orfE had no detectable effect on LOS or LPS production. The presence or absence of orfE in 36 isolates of C. jejuni did not correlate with LOS/LPS phenotype or serotype. However, after insertion of orfE into a LPS-producing orfE-negative strain the O-chain ladder was no longer detectable on Western blots. We were not able to disrupt the wbaP (rfbP) homologue (orfC) in C jejuni
Lipopolysaccharide, genetics, Campylobacter, mutation, distribution
NCBI PubMed ID: 10075420Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: ket!le.ac.uk
Institutions: Department of Genetics, University of Leicester, University Road, Leicester LE1 7RH, UK
Methods: PCR, DNA sequencing, SDS-PAGE
Expand this compound
Collapse this compound
2. Compound ID: 3256
a-L-QuipNAc-(1-3)-+
|
P-4)-a-L-QuipNAc-(1-3)-b-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-4)-D-Gal |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_153215,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1190
Senchenkova SN, Shashkov AS, Toukach FV, Ziolkowski A, Swierzko A, Amano K, Kaca W, Knirel YA, Kochetkov NK "Structure of the acid-labile galactosyl phosphate-containing O-antigen of Proteus vulgaris OX19 (serogroup O1) used in the Weil-Felix test" -
Biochemistry (Moscow) 62(5) (1997) 461-468
Lipopolysaccharide, LPS, structure, structural, polysaccharide, O-antigen, O antigen, phosphate, 2-acetamido-2, Proteus, serological, serology, serogroup, Glycosyl phosphate, Proteus vulgaris, Weil-Felix test, rickettsia, 6-dideoxy-L-glucose, diagnostic, Rickettsia japonica, test
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR
Expand this compound
Collapse this compound
3. Compound ID: 3257
a-L-QuipNAc-(1-3)-+
|
a-L-QuipNAc-(1-3)-b-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-4)-D-Gal |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_153215,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1190
Senchenkova SN, Shashkov AS, Toukach FV, Ziolkowski A, Swierzko A, Amano K, Kaca W, Knirel YA, Kochetkov NK "Structure of the acid-labile galactosyl phosphate-containing O-antigen of Proteus vulgaris OX19 (serogroup O1) used in the Weil-Felix test" -
Biochemistry (Moscow) 62(5) (1997) 461-468
Lipopolysaccharide, LPS, structure, structural, polysaccharide, O-antigen, O antigen, phosphate, 2-acetamido-2, Proteus, serological, serology, serogroup, Glycosyl phosphate, Proteus vulgaris, Weil-Felix test, rickettsia, 6-dideoxy-L-glucose, diagnostic, Rickettsia japonica, test
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR
Expand this compound
Collapse this compound
4. Compound ID: 3576
a-L-QuipNAc-(1-3)-+
|
P-4)-a-L-QuipNAc-(1-3)-a-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-4)-D-Gal |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_153215,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1332
Ziolkowski A, Shashkov AS, Swierzko A, Senchenkova SN, Toukach FV, Cedzynski M, Amano K, Kaca W, Knirel YA "Structures of the O-antigens of Proteus bacilli belonging to OX group (serogroups O1-O3) used in Weil-Felix test" -
FEBS Letters 411 (1997) 221-224
Structures of the O-specific polysaccharide chains of lipopolysaccharides from Proteus group OX strains (serogroups O1-O3) used as antigens in Weil-Felix test for diagnosis of rickettsiosis, were established. From them, the acid-labile polysaccharide of Proteus vulgaris OX19(O1) is built up of the following branched pentasaccharide repeating units connected via a phosphate group: [structure in text] where QuiNAc stands for 2-acetamido-2,6-dideoxyglucose (N-acetylquinovosamine). The basis of serospecificity of the Proteus group OX antigens and their cross-reactivity with human anti-rickettsial antibodies is discussed
Lipopolysaccharide, O-antigen, Proteus, bacterial polysaccharide structure, Serological cross-reactivity, Weil-Felix test, rickettsia, rickettsiosis
NCBI PubMed ID: 9271209Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: Center of Microbiology and Virology, Polish Academy of Sciences, Lodz, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Central Research Laboratory, Akita University, School of Medicine, Akita, Japan
Methods: NMR-2D, methylation, NMR, de-O-acetylation
Expand this compound
Collapse this compound
5. Compound ID: 3938
a-L-QuipNAc-(1-3)-+
|
P-4)-a-L-QuipNAc-(1-3)-b-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-4)-D-Galp |
Show graphically |
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_153215,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- 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
Expand this compound
Collapse this compound
6. Compound ID: 3945
b-D-GlcpNAc-(1-3)-+
|
-4)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GalpNAc-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_150899,IEDB_151531,IEDB_153215,IEDB_190606,IEDB_2218588,IEDB_885822,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- 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
Expand this compound
Collapse this compound
7. Compound ID: 5769
a-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
Show graphically |
Structure type: oligomer
Aglycon: Ceramide
Trivial name: glycosphingolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153215,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_3,SB_5,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2525
Leffler H, Svanborg-Eden C "Glycolipid receptors for uropathogenic Escherichia coli on human erythrocytes and uroepithelial cells" -
Infection and Immunity 34 (1981) 920-929
Journal NLM ID: 0246127Publisher: American Society for Microbiology
Expand this compound
Collapse this compound
8. Compound ID: 9136
b-D-GlcpNAc-(1-2)-b-D-Glcp-(1-2)-+
|
-4)-b-D-Galp-(1-3)-a-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-
|
b-D-GlcpNAc-(1-3)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391963,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_143260,IEDB_146664,IEDB_147450,IEDB_151531,IEDB_153215,IEDB_153218,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 3914
Parkhomchuk AA, Kocharova NA, Bialczak-Kokot M, Shashkov AS, Chizhov AO, Knirel YA, Rozalski A "Structure of the O-polysaccharide from the lipopolysaccharide of Providencia alcalifaciens O12" -
Carbohydrate Research 345(9) (2010) 1235-1239
The O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O12. Its structure was studied by sugar analysis using GLC of the alditol acetates and (S)-2-octyl glycosides, methylation analysis, Smith degradation, and (1)H and (13)C NMR spectroscopy, including 2D (1)H-(1)H COSY, TOCSY, ROESY, (1)H-(13)C HSQC, and HMBC experiments. It was found that the polymer is a neutral heteropolysaccharide and has a branched heptasaccharide repeating unit with the following structure: (formula, see text).
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, polysaccharide structure
NCBI PubMed ID: 20471004Publication DOI: 10.1016/j.carres.2010.04.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.A. Parhomchuk
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation
- 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
- Article ID: 5151
Du Y, Li H, Yin Z, Rozalski A, Torzewska A, Yang P, Qian C, Xu T, Cao H, Wu P, Jiang L, Guo X, Huang D, Liu B "Development of a molecular serotyping scheme and a multiplexed luminex-based array for Providencia" -
Journal of Microbiological Methods 153 (2018) 14-23
Providencia is an opportunistic human pathogen that belongs to the Enterobacteriaceae family. The bacterial cell surface O-antigen is one of the most structurally variable cell constituents and serves as a basis for serotyping gram-negative bacteria. In this work, the genomes of 12 Providencia strains were sequenced, and genes driving O-antigen biosynthesis were analyzed. The O-antigen-synthesizing genes of Providencia are located in the O-antigen gene cluster (OGC) between the cpxA and yibK genes. The gene functions predicted in silico agreed with the known O-antigen structures. All clusters were found to contain both wzx and wzy and exhibit a high degree of heterogeneity. Based on the sero-specific genes, we developed a molecular serotyping system to detect 23 serotypes (from the present and previous studies) for the first time. Five Proteus strains, five Morganella strains, five uropathogenic Escherichia coli (UPEC) strains and 32 Providencia strains with other serotypes were used to assess the specificity of our multiplexed Luminex-based array. Five serogroups (O3, O8, O19, O38 and O52 strains) were used to determine the sensitivity of the suspension array. The detection sensitivity was 0.1?ng genomic DNA, 103?CFU/ml in pure culture, or 104?CFU/ml in mock urine specimens. Furthermore, 29 publicly available Providencia genomes (which have not been serotyped) were analyzed, and 23 novel putative OGC types were identified. In total, we identified 35 new OGCs and developed a molecular serotyping system based on the sero-specific genes. The established classification system can support promising applications in basic research, clinical diagnosis, and epidemiological surveillance.
molecular, Providencia, O-antigen gene cluster, Molecular serotyping system, suspension array
NCBI PubMed ID: 30138644Publication DOI: 10.1016/j.mimet.2018.08.009Journal NLM ID: 8306883Correspondence: B. Liu
; D. Huang
Institutions: Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin Economic-Technological Development Area, Tianjin, China, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin Economic-Technological Development Area, Tianjin, China, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin Economic-Technological Development Area, Tianjin, China, Department of Biology of Bacteria, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland
Methods: PCR, DNA sequencing, genetic methods, serotyping
- 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
9. Compound ID: 11262
Structure type: oligomer
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153215,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4539
Jacobson JM, Kitov PI, Bundle DR "The synthesis of a multivalent heterobifunctional ligand for specific interaction with Shiga toxin 2 produced by E. coli O157:H7" -
Carbohydrate Research 378 (2013) 4-14
Hemolytic uremic syndrome is a potentially fatal complication of food poisoning caused by Escherichia coli O157:H7, especially those strains that produce the Stx2 Shiga toxin. Multivalent inhibitors based on the Pk trisaccharide are most effective against Stx1 the less dangerous of the two Shiga toxins. Inhibitors containing a terminal 2-acetamido-2-deoxy-α-D-galactopyranosyl residue in place of the terminal α-D-galactopyranosyl residue of Pk trisaccharide have been shown to exhibit preferential binding to Stx2. A multivalent heterobifunctional Pk analog containing 2-acetamido-2-deoxy-α-D-galactopyranose has been synthesized in a format that facilitates the ablation of toxin activity via supramolecular complex formation between Stx and the endogenous protein, Human serum amyloid P component (HuSAP).
Escherichia coli O157:H7, Glycomics, Shiga Toxin 2, Pk trisaccharide, Toxin inhibitors, Trisaccharide synthesis, Heterobifunctional ligand
NCBI PubMed ID: 23768952Publication DOI: 10.1016/j.carres.2013.05.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: dave.bundle@ualberta.ca (D.R. Bundle)
Institutions: Alberta Glycomics Centre, Department of Chemistry, University of Alberta, Edmonton, AB, Canada
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis
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: 4 sec