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1. Compound ID: 487
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 152
Varbanets L, Moskalenko N, Knirel Y, Kocharova N, Muras V, Chitchevitch N "Studies on the structure and activity of Burkholderia solanacearum lipopolysaccharides" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 484-489
Lipopolysaccharides (LPS) were isolated using the phenol-water procedure from 25 strains of Burkholderia (formerly Pseudomonas) solanacearum, belonging to biovars I-IV. Structures of O-specific polysaccharides (0-PS) were elucidated, using methylation analysis and NMR spectroscopy, including a computer-assisted 13C NMR-based analysis. Six distinct but related polysaccharide structures were identified. They have a backbone which consists of three L-rhamnopyranose residues and one residue of 2-acetamido-2-deoxy-D-glucopyranose and in some strains is substituted by a residue of L-xylopyranose or L-rhamnopyranose as a side chain. The 0-PS of most strains are not strictly regular and contain at least two types of structurally different oligosaccharide repeating units. Serological studies, using ELISA, revealed cross-reactivity between LPS of most of B. solanacearum strains investigated, thus indicating the occurrence of common antigenic determinants. At the same time, some antigenic differences were observed for LPS with structurally similar 0-PS chains which may be due to the presence of nonidentified minor components. The LPS showed a wide spectrum of pharmacological effects. It was found that LPS was able to extend the life of mice with experimental lymphoid and lymphocytic leukemia. B. solanacearum LPS expressed a broad antimetastatic effect. This was shown in a decrease of both volume and amount of metastases (for about 40 and 5 times, respectively) in mice with Lewis lung carcinoma. In mice with melanoma B-16 a lower level of LPS antimetastatic activity was found. We assume that in spite of the damage which 8. solanacearum induces in some agricultural plants its LPS may exert a pronounced positive action exhibiting antileukosic and antimetastatic effects.
Lipopolysaccharide, lipopolysaccharides, LPS, structure, Burkholderia, Pseudomonas, chain, group, O-polysaccharide, activity, Burkholderia solanacearum, pathogen, pathogens, pathovar, Pseudomonas solanacearum, Pseudomonas syringae
Publication DOI: 10.1007/978-94-011-5472-7_87Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: D.K.Zabolotny Institute of Microbiology and Virology, NAS of Ukraine, Zabolotnogo 154, Kiev Ukraine, N.D.Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russian Federation.
Methods: NMR, ELISA, GPC, phenol-water extraction
- Article ID: 404
Varbanets LD, Moskalenko NV, Kavun EM, Muras VA, Zhitkevich NV "Antigenic activity of Burkholderia solanacearum lipopolysaccharides" -
Biochemistry (Moscow) 61(5) (1996) 835-841
The interaction of the antiserum against Burkholderia solanacearum ICMP 8110 cells with lipopolysaccharides from 19 strains of B. solanacearum differing in O-polysaccharide structure has been studied using ELISA. No corellation was found between the O-polysaccharide structure and serological activity of the lipopolysaccharide. Most of lipopolysaccharides isolate from . B. solanacearum strains (exept for 4157, 767, and 7942) displayed cross-reactivity with the tested antiserum. These data indicate that the strains under study pertains to the same serogroup. It can not be excluded that some nonidentified components in the O-polysaccharide structure are responsible for the serological activity of the lipopolysaccharide.
lipopolysaccharides, Burkholderia, O-specific polysaccharide, activity, Burkholderia solanacearum, antigenic
NCBI PubMed ID: 8754270Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: DK Zabilotny Institute of Microbiology and Virologi, National Academy of Science of Ukraine, 252143 Kiev, ul Zabolotnogo, 154, AV Palladine Institute of Biochemistry, National Academy of Science of Ukraine, Kiev, Ukraine
Methods: ELISA
- Article ID: 1453
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1778
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
- Article ID: 2209
Kocharova NA, Knirel YA, Shashkov AS, Kochetkov NK, Varbanets LD "The structure of O-specific polysaccharide from Pseudomonas solanacearum ICMP 4157" -
Carbohydrate Research 228 (1992) 315-320
No abstract available
NCBI PubMed ID: 1381280Publication DOI: 10.1016/s0008-6215(00)90569-xJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, Smith degradation, GPC
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2. Compound ID: 1011
Structure type: oligomer
Trivial name: phospholipid (glycosylphosphopolyprenol)
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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3. Compound ID: 1012
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b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_1309625,IEDB_134619,IEDB_857717,IEDB_857718
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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4. Compound ID: 1014
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a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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5. Compound ID: 1015
|
a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
Show graphically |
Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_140116,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_857728,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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6. Compound ID: 1578
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-b-D-Araf-(1--/(->5) arabinan/ |
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Structure type: fragment of a bigger structure
Aglycon: (->5) arabinan
Trivial name: mannooligosaccharide cap of the LAM (ManLAM)
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164480,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 492
Nigou J, Gilleron M, Brando T, Puzo G "Structural analysis of mycobacterial lipoglycans" -
Applied Biochemistry and Biotechnology 118(1-3) (2004) 253-267
Mycobacterium tuberculosis, the causative agent of tuberculosis, is one of the most effective human pathogens. The mycobacterial cell envelope contains lipoglycans, and of particular interest is lipoarabinomannan (LAM), one of the most potent mycobacterial immunomodulatory molecules. The importance of lipoarabinomannan (LAM) in the immunopathogenesis of tuberculosis has incited structural studies on this molecule to (1) establish a precise structural model of the molecule and (2) decipher the structure/function relationships. In recent years, we have focused on the two domains essential for LAM biologic activities: the mannosyl-phosphatidyl-myo-inositol anchor and the caps. We review here the recent procedures developed for the structural analysis of these domains
structure, Mycobacterium, lipoarabinomannan, capillary electrophoresis, lipoglycan, nuclear magnetic resonance.
NCBI PubMed ID: 15304754Publication DOI: 10.1385/abab:118:1-3:253Journal NLM ID: 8208561Publisher: Humana Press
Correspondence: jerome.nigou@ipbs.fr
Institutions: Department of Molecular Mechanisms of Mycobacterial Infections, Institut de Pharmacologie et de Biologie Structurale, CNRS UMR 5089, 205, Route de Narbonne, 31077 Toulouse Cedex 4, France
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7. Compound ID: 1579
Structure type: fragment of a bigger structure
Aglycon: (->5) arabinan
Trivial name: phospho-myo-inositol cap (PILAM)
The structure is contained in the following publication(s):
- Article ID: 492
Nigou J, Gilleron M, Brando T, Puzo G "Structural analysis of mycobacterial lipoglycans" -
Applied Biochemistry and Biotechnology 118(1-3) (2004) 253-267
Mycobacterium tuberculosis, the causative agent of tuberculosis, is one of the most effective human pathogens. The mycobacterial cell envelope contains lipoglycans, and of particular interest is lipoarabinomannan (LAM), one of the most potent mycobacterial immunomodulatory molecules. The importance of lipoarabinomannan (LAM) in the immunopathogenesis of tuberculosis has incited structural studies on this molecule to (1) establish a precise structural model of the molecule and (2) decipher the structure/function relationships. In recent years, we have focused on the two domains essential for LAM biologic activities: the mannosyl-phosphatidyl-myo-inositol anchor and the caps. We review here the recent procedures developed for the structural analysis of these domains
structure, Mycobacterium, lipoarabinomannan, capillary electrophoresis, lipoglycan, nuclear magnetic resonance.
NCBI PubMed ID: 15304754Publication DOI: 10.1385/abab:118:1-3:253Journal NLM ID: 8208561Publisher: Humana Press
Correspondence: jerome.nigou@ipbs.fr
Institutions: Department of Molecular Mechanisms of Mycobacterial Infections, Institut de Pharmacologie et de Biologie Structurale, CNRS UMR 5089, 205, Route de Narbonne, 31077 Toulouse Cedex 4, France
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8. Compound ID: 2073
Structure type: polymer chemical repeating unit
Trivial name: neutral polysaccharide
Compound class: CPS
The structure is contained in the following publication(s):
- Article ID: 678
Hanniffy OM, Shashkov AS, Moran AP, Prendergast MM, Senchenkova SN, Knirel YA, Savage AV "Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O:41) containing only furanose sugars" -
Carbohydrate Research 319(1-4) (1999) 124-132
A neutral polysaccharide was obtained by hot phenol-water extraction of biomass from Campylobacter jejuni 176.83 and subsequently separated from acid-liberated core oligosaccharide of lipopolysaccharide by sequential GPC on Bio-Gel P6 and TSK-40 columns. All sugar components of the trisaccharide repeating unit of the polysaccharide were found to be of the furanose ring form. The major trisaccharide contained β-L-arabinose, 6-deoxy-β-D-altro-heptose (β-D-6d-altHep) and 6-deoxy-β-L-altrose (β-L-6d-Alt), whereas in the minor trisaccharide the β-L-6d-Alt is replaced by its C-5 epimer α-D-Fuc. On the basis of 1H and 13C NMR spectroscopic studies, including 2D ROESY, HMQC and HMQC-TOCSY experiments, the following structures of the repeating units were established: [formula: see text]
Campylobacter jejuni, L-Arabinose, O41 polysaccharide structure, 6-deoxy-D-altro-heptose, 6-Deoxy-L-altrose, D-fucose
NCBI PubMed ID: 10520260Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: angela.savage@nuigalway.ie
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland, Department of Chemistry, National University of Ireland, Galway, Ireland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow R- 17913, Russia
Methods: NMR-2D, NMR, acid hydrolysis
- Article ID: 1524
Karlyshev AV, Champion OL, Churcher C, Brisson JR, Jarrell HC, Gilbert M, Brochu D, St-Michael F, Li J, Wakarchuk WW, Goodhead I, Sanders M, Stevens K, White B, Parkhill J, Wren BW, Szymanski CM "Analysis of Campylobacter jejuni capsular loci reveals multiple mechanisms for the generation of structural diversity and the ability to form complex heptoses" -
Molecular Microbiology 55(1) (2005) 90-103
Summary We recently demonstrated that Campylobacter jejuni produces a capsular polysaccharide (CPS) that is the major antigenic component of the classical Penner serotyping system distinguishing Campylobacter into >60 groups. Although the wide variety of C. jejuni serotypes are suggestive of structural differences in CPS, the genetic mechanisms of such differences are unknown. In this study we sequenced biosynthetic cps regions, ranging in size from 15 to 34 kb, from selected C. jejuni strains of HS:1, HS:19, HS:23, HS:36, HS:23/36 and HS:41 serotypes. Comparison of the determined cps sequences of the HS:1, HS:19 and HS:41 strains with the sequenced strain, NCTC11168 (HS:2), provides evidence for multiple mechanisms of structural variation including exchange of capsular genes and entire clusters by horizontal transfer, gene duplication, deletion, fusion and contingency gene variation. In contrast, the HS:23, HS:36 and HS:23/36 cps sequences were highly conserved. We report the first detailed structural analysis of 81-176 (HS:23/36) and G1 (HS:1) and refine the previous structural interpretations of the HS:19, HS:23, HS:36 and HS:41 serostrains. For the first time, we demonstrate the commonality and function of a second heptose biosynthetic pathway for Campylobacter CPS independent of the pathway for lipooligosaccharide (LOS) biosynthesis and identify a novel heptosyltransferase utilized by this alternate pathway. Furthermore, we show the retention of two functional heptose isomerases in Campylobacter and the sharing of a phosphatase for both LOS and CPS heptose biosynthesis.
biosynthesis, Lipooligosaccharide, gene, LOS, capsular, capsular polysaccharide, Campylobacter jejuni, cluster, heptosyltransferase, serotyping, CPS, serotyping system, heptose biosynthesis
NCBI PubMed ID: 15612919Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: christine.szymanski@nrc-cnrc.gc.ca
Institutions: Department of Infectious and Tropical Diseases, London School of Hygiene and Tropical Medicine, London WCIE 7HT, UK, The Wellcome Trust Sanger Institute, The Wellcome Trust Genome Campus, Hinxton, Cambridge CB10 1SA, UK, Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, K1A 0R6
Methods: genetic methods
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9. Compound ID: 2125
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_142489,SB_86
The structure is contained in the following publication(s):
- Article ID: 678
Hanniffy OM, Shashkov AS, Moran AP, Prendergast MM, Senchenkova SN, Knirel YA, Savage AV "Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O:41) containing only furanose sugars" -
Carbohydrate Research 319(1-4) (1999) 124-132
A neutral polysaccharide was obtained by hot phenol-water extraction of biomass from Campylobacter jejuni 176.83 and subsequently separated from acid-liberated core oligosaccharide of lipopolysaccharide by sequential GPC on Bio-Gel P6 and TSK-40 columns. All sugar components of the trisaccharide repeating unit of the polysaccharide were found to be of the furanose ring form. The major trisaccharide contained β-L-arabinose, 6-deoxy-β-D-altro-heptose (β-D-6d-altHep) and 6-deoxy-β-L-altrose (β-L-6d-Alt), whereas in the minor trisaccharide the β-L-6d-Alt is replaced by its C-5 epimer α-D-Fuc. On the basis of 1H and 13C NMR spectroscopic studies, including 2D ROESY, HMQC and HMQC-TOCSY experiments, the following structures of the repeating units were established: [formula: see text]
Campylobacter jejuni, L-Arabinose, O41 polysaccharide structure, 6-deoxy-D-altro-heptose, 6-Deoxy-L-altrose, D-fucose
NCBI PubMed ID: 10520260Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: angela.savage@nuigalway.ie
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland, Department of Chemistry, National University of Ireland, Galway, Ireland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow R- 17913, Russia
Methods: NMR-2D, NMR, acid hydrolysis
- Article ID: 1524
Karlyshev AV, Champion OL, Churcher C, Brisson JR, Jarrell HC, Gilbert M, Brochu D, St-Michael F, Li J, Wakarchuk WW, Goodhead I, Sanders M, Stevens K, White B, Parkhill J, Wren BW, Szymanski CM "Analysis of Campylobacter jejuni capsular loci reveals multiple mechanisms for the generation of structural diversity and the ability to form complex heptoses" -
Molecular Microbiology 55(1) (2005) 90-103
Summary We recently demonstrated that Campylobacter jejuni produces a capsular polysaccharide (CPS) that is the major antigenic component of the classical Penner serotyping system distinguishing Campylobacter into >60 groups. Although the wide variety of C. jejuni serotypes are suggestive of structural differences in CPS, the genetic mechanisms of such differences are unknown. In this study we sequenced biosynthetic cps regions, ranging in size from 15 to 34 kb, from selected C. jejuni strains of HS:1, HS:19, HS:23, HS:36, HS:23/36 and HS:41 serotypes. Comparison of the determined cps sequences of the HS:1, HS:19 and HS:41 strains with the sequenced strain, NCTC11168 (HS:2), provides evidence for multiple mechanisms of structural variation including exchange of capsular genes and entire clusters by horizontal transfer, gene duplication, deletion, fusion and contingency gene variation. In contrast, the HS:23, HS:36 and HS:23/36 cps sequences were highly conserved. We report the first detailed structural analysis of 81-176 (HS:23/36) and G1 (HS:1) and refine the previous structural interpretations of the HS:19, HS:23, HS:36 and HS:41 serostrains. For the first time, we demonstrate the commonality and function of a second heptose biosynthetic pathway for Campylobacter CPS independent of the pathway for lipooligosaccharide (LOS) biosynthesis and identify a novel heptosyltransferase utilized by this alternate pathway. Furthermore, we show the retention of two functional heptose isomerases in Campylobacter and the sharing of a phosphatase for both LOS and CPS heptose biosynthesis.
biosynthesis, Lipooligosaccharide, gene, LOS, capsular, capsular polysaccharide, Campylobacter jejuni, cluster, heptosyltransferase, serotyping, CPS, serotyping system, heptose biosynthesis
NCBI PubMed ID: 15612919Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: christine.szymanski@nrc-cnrc.gc.ca
Institutions: Department of Infectious and Tropical Diseases, London School of Hygiene and Tropical Medicine, London WCIE 7HT, UK, The Wellcome Trust Sanger Institute, The Wellcome Trust Genome Campus, Hinxton, Cambridge CB10 1SA, UK, Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, K1A 0R6
Methods: genetic methods
- Article ID: 5449
Huddleston JP, Raushel FM "Biosynthesis of GDP-d-glycero-α-d-manno-heptose for the Capsular Polysaccharide of Campylobacter jejuni" -
Biochemistry 58(37) (2019) 3893-3902
The capsular polysaccharide (CPS) structure of Campylobacter jejuni contributes to its robust fitness. Many strains contain heptose moieties in their CPS units. The precursor heptose is GDP-d-glycero-α-d-manno-heptose; modifications to the stereochemistry at C3-C6 as well as additions of methyl and phosphoramidate groups lend to the hypervariability of the C. jejuni CPS structures. Synthesis of GDP-d-glycero-α-d-manno-heptose has been described previously, but using enzymes from Aneurinibacillus thermoaerophilus DSM 10155. Here we describe the complete synthesis of GDP-d-glycero-α-d-manno-heptose using enzymes from C. jejuni NTCC 11168: Cj1152 and Cj1423-Cj1425. Our results yield kinetic parameters for these enzymes and outline a successful strategy for milligram-gram scale synthesis of GDP-d-glycero-α-d-manno-heptose. This achievement is critical for the characterization of other carbohydrate tailoring enzymes, which are expected to utilize GDP-d-glycero-α-d-manno-heptose for the biosynthesis of more complex carbohydrates in the CPS of C. jejuni.
biosynthesis, synthesis, structure, heptose, capsular polysaccharide, Campylobacter jejuni, modification, Enzymes, phosphoramidate, stereochemistry
NCBI PubMed ID: 31449400Publication DOI: 10.1021/acs.biochem.9b00548Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: raushel@tamu.edu
Institutions: Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
Methods: 13C NMR, 1H NMR, kinetics assays, 31P NMR, anion-exchange chromatography, MS, genetic methods, HPLC, UV, cloning, bioinformatic analysis, enzymatic synthesis
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10. Compound ID: 2253
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf-(1--/polymer of -5)aDAraf(1-/ |
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Structure type: oligomer
Aglycon: polymer of -5)aDAraf(1-
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_857727,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 743
Khoo KH, Tang JB, Chatterjee D "Variation in mannose-capped terminal arabinan motifs of lipoarabinomannans from clinical isolates of Mycobacterium tuberculosis and Mycobacterium avium complex" -
Journal of Biological Chemistry 276(6) (2001) 3863-3871
The unique terminal arabinan motifs of mycobacterial lipoarabinomannan (LAM), which are mannose-capped to different extents, probably constitute the single most important structural entity engaged in receptor binding and subsequent immunopathogenesis. We have developed a concerted approach of endoarabinanase digestion coupled with chromatography and mass spectrometry analysis to rapidly identify and quantitatively map the complement of such terminal units among the clinical isolates of different virulence and drug resistance profiles. In comparison with LAM from laboratory strains of Mycobacterium tuberculosis, an ethambutol (Emb) resistant clinical isolate was shown to have a significantly higher proportion of nonmannose capped arabinan termini. More drastically, the mannose capping was completely inhibited when an Emb-susceptible strain was grown in the presence of subminimal inhibitory concentration of Emb. Both cases resulted in an increase of arabinose to mannose ratio in the overall glycosyl composition of LAM. Emb, therefore, not only could affect the complete elaboration of the arabinan as found previously for LAM from Mycobacterium smegmatis resistant mutant but also could inhibit the extent of mannose capping and hence its associated biological functions in M. tuberculosis. Unexpectedly, an intrinsically Emb-resistant Mycobacterium avium isolate of smooth transparent colony morphology was found to have most of its arabinan termini capped with a single mannose residue instead of the more common dimannoside as established for LAM from M. tuberculosis. This is the first report on the LAM structure from M. avium complex, an increasingly important opportunistic infectious agent afflicting AIDS patients
structure, virulence, lipoarabinomannan, Mycobacterium tuberculosis, tuberculosis, Mycobacterium avium Complex
NCBI PubMed ID: 11073941Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523, USA
Methods: HPAEC, MS, enzymatic digestion
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11. Compound ID: 2254
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1--/polymer of -5)aDAraf(1-/ |
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Structure type: oligomer
Aglycon: polymer of -5)aDAraf(1-
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 743
Khoo KH, Tang JB, Chatterjee D "Variation in mannose-capped terminal arabinan motifs of lipoarabinomannans from clinical isolates of Mycobacterium tuberculosis and Mycobacterium avium complex" -
Journal of Biological Chemistry 276(6) (2001) 3863-3871
The unique terminal arabinan motifs of mycobacterial lipoarabinomannan (LAM), which are mannose-capped to different extents, probably constitute the single most important structural entity engaged in receptor binding and subsequent immunopathogenesis. We have developed a concerted approach of endoarabinanase digestion coupled with chromatography and mass spectrometry analysis to rapidly identify and quantitatively map the complement of such terminal units among the clinical isolates of different virulence and drug resistance profiles. In comparison with LAM from laboratory strains of Mycobacterium tuberculosis, an ethambutol (Emb) resistant clinical isolate was shown to have a significantly higher proportion of nonmannose capped arabinan termini. More drastically, the mannose capping was completely inhibited when an Emb-susceptible strain was grown in the presence of subminimal inhibitory concentration of Emb. Both cases resulted in an increase of arabinose to mannose ratio in the overall glycosyl composition of LAM. Emb, therefore, not only could affect the complete elaboration of the arabinan as found previously for LAM from Mycobacterium smegmatis resistant mutant but also could inhibit the extent of mannose capping and hence its associated biological functions in M. tuberculosis. Unexpectedly, an intrinsically Emb-resistant Mycobacterium avium isolate of smooth transparent colony morphology was found to have most of its arabinan termini capped with a single mannose residue instead of the more common dimannoside as established for LAM from M. tuberculosis. This is the first report on the LAM structure from M. avium complex, an increasingly important opportunistic infectious agent afflicting AIDS patients
structure, virulence, lipoarabinomannan, Mycobacterium tuberculosis, tuberculosis, Mycobacterium avium Complex
NCBI PubMed ID: 11073941Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523, USA
Methods: HPAEC, MS, enzymatic digestion
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12. Compound ID: 3409
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b-L-Araf-(1-6)-+
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a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1-2)-b-D-Galf-(1-3)-b-L-Araf-(1-1)-Thre-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114709,IEDB_135813,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_151531,IEDB_190606
The structure is contained in the following publication(s):
- Article ID: 1244
Sorum U, Robertsen B, Kenne L "Structural studies of the major polysaccharide in the cell wall of Renibacterium salmoninarum" -
Carbohydrate Research 306(1-2) (1998) 305-314
The galactose-rich polysaccharide (GPS) in the cell wall of the Gram-positive bacterium Renibacterium salmoninarum, the causative agent in of bacterial kidney disease (BKD) of salmonids, has been studied by sugar and methylation analysis, partial acid hydrolysis, Smith degradation, FABMS, and 1H and 13C NMR spectroscopy. The data show that the GPS has a heptasaccharide repeating unit with the following structure: α-D-Rhap-(1→3)-α-L-FucpNAc-(1→)-β-D-GlcpNAc 1 decreases 2 →3)-β-D-Galf-(1→6)-β-D-Galf-(1→3)-β-D-Galf-(1→6)-β-D-Galf-(1→.
NMR, structure, cell wall polysaccharide, Renibacterium salmoninarum
NCBI PubMed ID: 9691455Publication DOI: 10.1016/s0008-6215(97)10071-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Marine Biochemistry, The Norwegian College of Fishery Science, University of Tromsø, N-9037 Tromsø, Norway, Department of Chemistry, Swedish University of Agricultural Sciences, Box 7015, S-750 07 Uppsala, Sweden
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, partial acid hydrolysis, Smith degradation
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13. Compound ID: 3741
Structure type: polymer chemical repeating unit
Trivial name: LAM
The structure is contained in the following publication(s):
- Article ID: 698
Guerardel Y, Maes E, Elass E, Leroy Y, Timmerman P, Besra GS, Locht C, Strecker G, Kremer L "Structural study of lipomannan and lipoarabinomannan from Mycobacterium chelonae. Presence of unusual components with α1,3-mannopyranose side chains" -
Journal of Biological Chemistry 277(34) (2002) 30635-30648
Lipomannan (LM) and lipoarabinomannan (LAM) are major glycolipids present in the mycobacterial cell wall that are able to modulate the host immune response. In this study, we have undertaken the structural determination of these important modulins in Mycobacterium chelonae, a fast growing pathogenic mycobacterial species. One-dimensional and two-dimensional NMR spectra were used to demonstrate that LM and LAM from M. chelonae, designated CheLM and CheLAM, respectively, possess structures that differ from the ones reported earlier in other mycobacterial species. Analysis by gas chromatography/mass spectrometry of the phosphatidyl-myo-inositol anchor, which is thought to play a role in the biological functions of these lipoglycans, pointed to a high degree of heterogeneity based on numerous combinations of acyl groups on the C-1 and C-2 positions of the glycerol moiety. Characterization of the mannan core of CheLM and CheLAM revealed the presence of novel α1,3-mannopyranosyl side chains. This motif, which reacted specifically with the lectin from Galanthus nivalis, was found to be unique among a panel of nine mycobacterial species. Then, CheLM and CheLAM were found to be devoid of both the mannooligosaccharide cap present in Mycobacterium tuberculosis and the inositol phosphate cap present in Mycobacterium smegmatis and other fast growing species. Tumor necrosis factor-alpha and interleukin-8 production were assessed from human macrophages with LAM preparations from different species. Our results suggest that the inositol phosphate capping may represent the major cytokine-inducing component of LAMs. This work not only underlines the diversity of LAM structures among various mycobacterial species but also provides new structures that could be useful to dissect the structure-function relationships of these complex molecules.
lipopolysaccharides, antigens, cell wall, structural studies, Mycobacterium, glycolipid, immune response, lipoarabinomannan, tumor necrosis factor, CD1, interleukin-8, lectins, Mycobacterium chelonae
NCBI PubMed ID: 12063260Publication DOI: 10.1074/jbc.M204398200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: laurent.kremer@ibl.fr
Institutions: Laboratoire de Glycobiologie Structurale et Fonctionnelle, CNRS UMR8576, Universite des Sciences et Technologies de Lille, F-59655 Villeneuve Ascq Cedex, France, School of Biosciences, University of Birmingham, Edgbaston, Birmingham, B15 2TT United Kingdom, Laboratoire des Mecanismes Moleculaires de la Pathogenie
Methods: NMR-2D, NMR, MALDI-MS
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14. Compound ID: 3802
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: arabinan in LAM
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_857727,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1450
Chatterjee D, Khoo K "Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects" -
Glycobiology 8(2) (1998) 113-120
Detailed structural and functional studies over the last decade have led to current recognition of the mycobacterial lipoarabinomannan (LAM) as a phosphatidylinositol anchored lipoglycan with diverse biological activities. Fatty acylation has been demonstrated to be essential for LAM to maintain its functional integrity although the focus has largely been on the arabinan motifs and the terminal capping function. It has recently been shown that the mannose caps may be involved not only in attenuating host immune response, but also in mediating the binding of mycobacteria to and subsequent entry into macrophages. This may further be linked to an intracellular trafficking pathway through which LAM is thought to be presented by CD1 to subsets of T-cells. The implication of LAM as major histocompatibility complex (MHC)-independent T-cell epitope and the ensuing immune response is an area of intensive studies. Another recent focus of research is the biosynthesis of arabinan which has been shown to be inhibitable by the anti-tuberculosis drug, ethambutol. The phenomenon of truncated LAM as synthesized by ethambutol resistant strains provides an invaluable handle for dissecting the array of arabinosyltransferases involved, as well as generating much needed structural variants for further structural and functional studies. It is hoped that with more systematic investigations based on clinical isolates and human cell lines, the true significance of LAM in the immunopathogenesis of tuberculosis and leprosy can eventually be explained.
structure, Mycobacteria, lipoarabinomannan, lipoglycan, tuberculosis, CD1, phosphatidylinositol, ethambutol, lipomannan, phosphatidylinositol mannosides
NCBI PubMed ID: 9451020Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO 80523, USA and Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
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15. Compound ID: 3803
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: structural motif or average structure
Trivial name: arabinan in LAM
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1450
Chatterjee D, Khoo K "Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects" -
Glycobiology 8(2) (1998) 113-120
Detailed structural and functional studies over the last decade have led to current recognition of the mycobacterial lipoarabinomannan (LAM) as a phosphatidylinositol anchored lipoglycan with diverse biological activities. Fatty acylation has been demonstrated to be essential for LAM to maintain its functional integrity although the focus has largely been on the arabinan motifs and the terminal capping function. It has recently been shown that the mannose caps may be involved not only in attenuating host immune response, but also in mediating the binding of mycobacteria to and subsequent entry into macrophages. This may further be linked to an intracellular trafficking pathway through which LAM is thought to be presented by CD1 to subsets of T-cells. The implication of LAM as major histocompatibility complex (MHC)-independent T-cell epitope and the ensuing immune response is an area of intensive studies. Another recent focus of research is the biosynthesis of arabinan which has been shown to be inhibitable by the anti-tuberculosis drug, ethambutol. The phenomenon of truncated LAM as synthesized by ethambutol resistant strains provides an invaluable handle for dissecting the array of arabinosyltransferases involved, as well as generating much needed structural variants for further structural and functional studies. It is hoped that with more systematic investigations based on clinical isolates and human cell lines, the true significance of LAM in the immunopathogenesis of tuberculosis and leprosy can eventually be explained.
structure, Mycobacteria, lipoarabinomannan, lipoglycan, tuberculosis, CD1, phosphatidylinositol, ethambutol, lipomannan, phosphatidylinositol mannosides
NCBI PubMed ID: 9451020Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO 80523, USA and Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
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Next 15 structure(s)
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Total list of corresponding CSDB IDs (permanent record IDs):
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