Found 36 structures.
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1. Compound ID: 722
|
Asp-(1-2)-+
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a-L-Rhap2Me-(1-4)-+ |
| |
b-D-GlcpNAcA4Me-(1-4)-b-D-GlcpA-(1-4)-b-D-Xylp2Ac3Ac-(1-4)-a-D-GlcpA2Me-(1-2)-a-D-Manp-(1-3)-Ser-(1-2)-Ala-(1-2)-Ala |
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Structure type: oligomer
Trivial name: glycopeptide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_130701,IEDB_136105,IEDB_140630,IEDB_144983,IEDB_150900,IEDB_152206,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov E, Perry MB, Kay WW "The structure of the glycopeptides from the fish pathogen Flavobacterium columnare" -
Carbohydrate Research 338(23) (2003) 2653-2658
Proteolytic digestion of the phenol-water extraction product of the fish pathogen Flavobacterium columnare afforded a mixture of glycopeptides in which the oligosaccharide moiety was an unusual hexasaccharide composed of 4-O-methyl-2-acetamido-2-deoxy-D-glucuronic acid (GlcNAcA), D-glucuronic acid (D-GlcA), 2,3-di-O-acetyl-D-xylose (D-Xyl), 2-O-methyl-D-glucuronic acid (D-GlcA), D-mannose (D-Man), and 2-O-methyl-L-rhamnose (L-Rha). By the application of high-resolution 1D and 2D NMR, mass spectrometry, and chemical analysis, the hexasaccharide structure was determined to be: [carbohydrate structure--see text] where all monosaccharides have the D-configuration except for 2-O-methyl-L-rhamnose; and were in the pyranose form. Only one carbohydrate structure was found. The peptide part was represented by tri- to hepta-peptides with a minimal common tripeptide fragment Asp-Ser-Ala, extended with Ala and Val
NMR, MS, Flavobacterium columnare, glycopeptide
NCBI PubMed ID: 14670723Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6, Department of Bacteriology and Biochemistry, University of Victoria, Victoria, BC, Canada V8W 2T2
Methods: NMR-2D, NMR, chemical analysis, MS
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2. Compound ID: 750
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 198
Vinogradov EV, Petersen BO, Thomas-Oates JE, Duus JO, Brade H, Holst O "Characterization of a novel branched tetrasaccharide of 3-deoxy-D-manno-oct-2-ulopyranosonic acid. The structure of the carbohydrate backbone of the lipopolyasccharide from Acinetobacter baumannii strain NCTC 10303 (ATCC 17904)" -
Journal of Biological Chemistry 273(43) (1998) 28122-28131
For the first time, the tetrasaccharide Kdo a2→5 Kdo a2→5 (Kdo a2→4)Kdo (Kdo is 3-deoxy-Dmanno-oct-2-ulopyranosonic acid) has been identified in a bacterial lipopolysaccharide (LPS), i.e. in the core region of LPS from Acinetobacter baumannii NCTC 10303. The LPS was analyzed using compositional analysis, mass spectrometry, and NMR spectroscopy. The disaccharide DGlcpN b1→6 DGlcpN, phosphorylated at O-1 and O-4', was identified as the carbohydrate backbone of the lipid A. The Kdo tetrasaccharide is attached to O-6' of this disaccharide and is further substituted by short L-rhamnoglycans of varying length and by the disaccharide DGlcpNAc a1→4 DGlcpNA (GlcpNA, 2-amino-2-deoxy-glucopyranosuronic acid). The core region is not substituted by phosphate residues and represents a novel core type of bacterial LPS. The complete carbohydrate backbone of the LPS is shown in Structure I as follows: [see formula in text] where Rha is rhamnose. Except were indicated, monosaccharides possess the D-configuration. Sugars marked with an asterisk are present in non-stoichiometric amounts.
LPS, structure, core, acid, Acinetobacter, Acinetobacter baumannii, 3-deoxy-D-manno-oct-2-ulopyranosonic
NCBI PubMed ID: 9774431Publication DOI: 10.1074/jbc.273.43.28122Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: oholst@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, D-23845 Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, DK-2500 Valby, Denmark, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Utrecht University,NL-3584 CA Utrecht, The Netherlands
Methods: NMR-2D, NMR, MS, composition analysis
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3. Compound ID: 1190
Structure type: polymer chemical repeating unit
Compound class: CPS
The structure is contained in the following publication(s):
- Article ID: 367
Sau S, Lee CY "Cloning of type 8 capsule genes and analysis of gene clusters for the production of different capsular polysaccharides in Staphylococcus aureus" -
Journal of Bacteriology 178(7) (1996) 2118-2126
Eleven serotypes of capsular polysaccharide from Staphylococcus aureus have been reported. We have previously cloned a cluster of type 1 capsule (cap1) genes responsible for type 1 capsular polysaccharide biosynthesis in S. aureus M. To clone the type 8 capsule (cap8) genes, a plasmid library of type 8 strain Becker was screened with a labelled DNA fragment containing the cap1 genes under low-stringency conditions. One recombinant plasmid containing a 14-kb insert was chosen for further study and found to complement 14 of the 18 type 8 capsule-negative (Cap8-) mutants used in the study. Additional library screening, subcloning, and complementation experiments showed that all of the 18 Cap8- mutants were complemented by DNA fragments derived from a 20.5-kb contiguous region of the Becker chromosome. The mutants were mapped into six complementation groups, indicating that the cap8 genes are clustered. By Southern hybridization analyses under high-stringency conditions, we found that DNA fragments containing the cap8 gene cluster show extensive homology with all 17 strains tested, including type 1 strains. By further Southern analyses and cloning of the cap8-related homolog from strain M, we show that strain M carries an additional capsule gene cluster different from the cap1 gene cluster. In addition, by using DNA fragments containing different regions of the cap8 gene cluster as probes to hybridize DNA from different strains, we found that the central region of the cap8 gene cluster hybridizes only to DNAs from certain strains tested whereas the flanking regions hybridize to DNAs of all strains tested. Thus, the cap8 gene clusters and its closely related homologs are likely to have organizations similar to those of the encapsulation genes of other bacterial systems.
capsular polysaccharides, analysis, cloning, type, gene cluster, capsule, Staphylococcus aureus
NCBI PubMed ID: 8606192Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: clee@kumc.edu
Institutions: Department of Microbiology, Molecular Genetics and Immunology, University of Kansas Medical Center, Kansas City, Kansas 66160
Methods: genetic methods
- Article ID: 3296
Lee JC, Xu S, Albus A, Livolsi PJ "Genetic analysis of type 5 capsular polysaccharide expression by Staphylococcus aureus" -
Journal of Bacteriology 176(16) (1994) 4883-4889
Capsules are produced by over 90% of Staphylococcus aureus strains, and approximately 25% of clinical isolates express type 5 capsular polysaccharide (CP5). We mutagenized the type 5 strain Reynolds with Tn918 to target genes involved in CP5 expression. From a capsule-deficient mutant, we cloned into a cosmid vector an approximately 26-kb EcoRI fragment containing the transposon insertion. In the absence of tetracycline selection, Tn918 was spontaneously excised, thereby resulting in a plasmid containing 9.4 kb of S. aureus DNA flanking the Tn918 insertion site. The 9.4-kb DNA fragment was used to screen a cosmid library prepared from the wild-type strain. Positive colonies were identified by colony hybridization, and a restriction map of one clone (pJCL19 with an approximately 34-kb insert) carrying the putative capsule gene region was constructed. Fragments of pJCL19 were used to probe genomic DNA digests from S. aureus strains of different capsular serotypes. Fragments on the ends of the cloned DNA hybridized to fragments of similar sizes in most of the strains examined. Blots hybridized to two fragments flanking the central region of the cloned DNA showed restriction fragment length polymorphism. A centrally located DNA fragment hybridized only to DNA from capsular types 2, 4, and 5. DNA from pJCL19 was subcloned to a shuttle vector for complementation studies. A 6.2-kb EcoRI-ClaI fragment complemented CP5 expression in a capsule-negative mutant derived by mutagenesis with ethyl methanesulfonate. These experiments provide the necessary groundwork for identifying genes involved in CP5 expression by S. aureus.
genetic, clinical, expression, gene, genetics, DNA, strain, capsular, polysaccharide, serotype, analysis, capsular polysaccharide, type, mutant, region, insertion, plasmid, capsule, Staphylococcus, Staphylococcus aureus, fragment, Serotypes, site, clone, PDF, capsules, selection, polymorphism
NCBI PubMed ID: 805001Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Boston, Massachusetts.
Methods: serological methods, genetic methods
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4. Compound ID: 2745
|
-4)-b-D-GlcpNAcA3Ac-(1-4)-a-L-FucpNAm3Ac-(1-3)-a-D-6dxylHexpN-4-ulo-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 961
MacLean LL, Perry MB, Crump EM, Kay WW "Structural characterization of the lipopolysaccharide O-polysaccharide antigen produced by Flavobacterium columnare ATCC43622 Leann L. MacLean, Malcolm B. Perry, Elizabeth M. Crump, William W. Kay" -
European Journal of Biochemistry 270(16) (2003) 3440-3446
The structure of the antigenic O-chain polysaccharide of Flavobacterium columnare ATCC43622, a Gram-negative bacterium that causes columnaris disease in warm water fish, was determined by high-field 1D and 2D NMR techniques, MS, and chemical analyses. The O-chain was shown to be an unbranched linear polymer of a trisaccharide repeating unit composed of 2-acetamido-2-deoxy-d-glucuronic acid (d-GlcNAcA), 2-acetamidino-2,6-dideoxy-l-galactose (l-FucNAm) and 2-acetamido-2,6-dideoxy-d-xylo-hexos-4-ulose (d-Sug) (1 : 1 : 1), having the structure: [structure: see text].
Lipopolysaccharide, antigen, structural, characterization, O-polysaccharide, O polysaccharide, Flavobacterium
NCBI PubMed ID: 12899701Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: malcolm.perry@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, Department of Biochemistry and Microbiology, University of Victoria, Victoria, British Columbia, Canada
Methods: NMR-2D, NMR, chemical analysis, MS
- Article ID: 6301
Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" -
Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.
chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal
NCBI PubMed ID: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
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5. Compound ID: 2746
|
-4)-b-D-GlcpNAcA-(1-4)-a-L-FucpNAm-(1-3)-a-D-6dxylHexpN-4-ulo-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
The structure is contained in the following publication(s):
- Article ID: 961
MacLean LL, Perry MB, Crump EM, Kay WW "Structural characterization of the lipopolysaccharide O-polysaccharide antigen produced by Flavobacterium columnare ATCC43622 Leann L. MacLean, Malcolm B. Perry, Elizabeth M. Crump, William W. Kay" -
European Journal of Biochemistry 270(16) (2003) 3440-3446
The structure of the antigenic O-chain polysaccharide of Flavobacterium columnare ATCC43622, a Gram-negative bacterium that causes columnaris disease in warm water fish, was determined by high-field 1D and 2D NMR techniques, MS, and chemical analyses. The O-chain was shown to be an unbranched linear polymer of a trisaccharide repeating unit composed of 2-acetamido-2-deoxy-d-glucuronic acid (d-GlcNAcA), 2-acetamidino-2,6-dideoxy-l-galactose (l-FucNAm) and 2-acetamido-2,6-dideoxy-d-xylo-hexos-4-ulose (d-Sug) (1 : 1 : 1), having the structure: [structure: see text].
Lipopolysaccharide, antigen, structural, characterization, O-polysaccharide, O polysaccharide, Flavobacterium
NCBI PubMed ID: 12899701Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: malcolm.perry@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, Department of Biochemistry and Microbiology, University of Victoria, Victoria, British Columbia, Canada
Methods: NMR-2D, NMR, chemical analysis, MS
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6. Compound ID: 3018
|
S-3)-+
|
-4)-b-D-GlcpNAcA-(1-6)-a-D-Manp-(1-4)-b-D-GlcpNAcA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1083
Parolis H, Parolis LAS, Boán IF, Rodríguez-Valera F, Widmalm G, Manca MC, Jansson P, Sutherland IW "The structure of the exopolysaccharide produced by the halophilic Archaeon Haloferax mediterranei strain R4 (ATCC33500)" -
Carbohydrate Research 295 (1996) 147-156
The halophilic Archaeon Haloferax mediterranei exudes into the growth medium a high molecular weight sulfated polysaccharide. The structure of the repeating unit of this polymer was determined by a combination of glycose, methylation, and sulfate analysis, periodate oxidation, and 1D and 2D NMR spectroscopic analysis of the native and periodate-oxidised/reduced polysaccharides. The location of the sulfate group was established from the 1H and 13C NMR data. The structure of the repeating unit of the polysaccharide may be written as [formula: see text]
structure, strain, exopolysaccharide, sulfate, Archaeon, Haloferax, halophilic
NCBI PubMed ID: 9002190Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, School of Pharmaceutical Sciences, Rhodes University, Grahamstown, 6140, South Africa, Departamento de Genetica y Microbiologia, Universidad de Alicante, Campus de San Juan, Apdo. 374, E-03080 Alicante, Spain, Clinical Research centre, Analytical Unit, Karolinska Institute, Huddinge Hospital, Huddinge, Sweden, Institute of Cell and Molecular Biology, Edingurgh University, Mayfield Rd. Edingurgh, EH9 3JH, UK
Methods: methylation, periodate oxidation, NMR-2D, NMR, sugar analysis, sulfate analysis
- Article ID: 5137
Casillo A, Lanzetta R, Parrilli M, Corsaro MM "Exopolysaccharides from Marine and Marine Extremophilic Bacteria: Structures, Properties, Ecological Roles and Applications" -
Marine Drugs 16(2) (2018) pii E69
The marine environment is the largest aquatic ecosystem on Earth and it harbours microorganisms responsible for more than 50% of total biomass of prokaryotes in the world. All these microorganisms produce extracellular polymers that constitute a substantial part of the dissolved organic carbon, often in the form of exopolysaccharides (EPS). In addition, the production of these polymers is often correlated to the establishment of the biofilm growth mode, during which they are important matrix components. Their functions include adhesion and colonization of surfaces, protection of the bacterial cells and support for biochemical interactions between the bacteria and the surrounding environment. The aim of this review is to present a summary of the status of the research about the structures of exopolysaccharides from marine bacteria, including capsular, medium released and biofilm embedded polysaccharides. Moreover, ecological roles of these polymers, especially for those isolated from extreme ecological niches (deep-sea hydrothermal vents, polar regions, hypersaline ponds, etc.), are reported. Finally, relationships between the structure and the function of the exopolysaccharides are discussed.
NMR, capsular polysaccharide, exopolysaccharide, exopolysaccharides, EPS, purification, Extremophile, marine, chemical characterization, GC-MS, structure/activity relationship
NCBI PubMed ID: 29461505Publication DOI: 10.3390/md16020069Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: corsaro@unina.it; angela.casillo@unina.it
Institutions: Department of Chemical Sciences, University of Naples 'Federico II', Naples 80126, Italy
- Article ID: 5253
Vijayendra SV, Shamala TR "Film forming microbial biopolymers for commercial applications-A review" -
Critical Reviews in Biotechnology 34(4) (2014) 338-357
Microorganisms synthesize intracellular, structural and extracellular polymers also referred to as biopolymers for their function and survival. These biopolymers play specific roles as energy reserve materials, protective agents, aid in cell functioning, the establishment of symbiosis, osmotic adaptation and support the microbial genera to function, adapt, multiply and survive efficiently under changing environmental conditions. Viscosifying, gelling and film forming properties of these have been exploited for specific significant applications in food and allied industries. Intensive research activities and recent achievements in relevant and important research fields of global interest regarding film forming microbial biopolymers is the subject of this review. Microbial polymers such as pullulan, kefiran, bacterial cellulose (BC), gellan and levan are placed under the category of exopolysaccharides (EPS) and have several other functional properties including film formation, which can be used for various applications in food and allied industries. In addition to EPS, innumerable bacterial genera are found to synthesis carbon energy reserves in their cells known as polyhydroxyalkanoates (PHAs), microbial polyesters, which can be extruded into films with excellent moisture and oxygen barrier properties. Blow moldable biopolymers like PHA along with polylactic acid (PLA) synthesized chemically in vitro using lactic acid (LA), which is produced by LA bacteria through fermentation, are projected as biodegradable polymers of the future for packaging applications. Designing and creating of new property based on requirements through controlled synthesis can lead to improvement in properties of existing polysaccharides and create novel biopolymers of great commercial interest and value for wider applications. Incorporation of antimicrobials such as bacteriocins or silver and copper nanoparticles can enhance the functionality of polymer films especially in food packaging applications either in the form of coatings or wrappings. Use of EPS in combinations to obtain desired properties can be evaluated to increase the application range. Controlled release of active compounds, bioactive protection and resistance to water can be investigated while developing new technologies to improve the film properties of active packaging and coatings. An holistic approach may be adopted in developing an economical and biodegradable packaging material with acceptable properties. An interdisciplinary approach with new innovations can lead to the development of new composites of these biopolymers to enhance the application range. This current review focuses on linking and consolidation of recent research activities on the production and applications of film forming microbial polymers like EPS, PHA and PLA for commercial applications. © 2014 Informa Healthcare USA, Inc.
exopolysaccharides, fermentation, antimicrobial films, biodegradable, polyhydroxyalkanoates, polylactic acid
NCBI PubMed ID: 23919238Publication DOI: 10.3109/07388551.2013.798254Journal NLM ID: 8505177Publisher: CRC Press
Correspondence: Vijayendra SV
; Vijayendra SV
Institutions: Food Microbiology Department, CSIR-Central Food Technological Research Institute (A constituent laboratory of Council of Scientific and Industrial Research, New Delhi), Mysore, Karnataka, India
- Article ID: 5444
Hamidi M, Mirzaei R, Delattre C, Khanaki K, Pierre G, Gardarin C, Petit E, Karimitabar F, Faezi S "Characterization of a new exopolysaccharide produced by Halorubrum sp. TBZ112 and evaluation of its anti-proliferative effect on gastric cancer cells" -
3 Biotech 9(1) (2019) 1
In the present study, we aimed to extract, purify, analyze monosaccharide composition of exopolysaccharide (EPS) produced by Halorubrum sp. TBZ112 (KCTC 4203 and IBRC-M 10773) and also to evaluate its possible antiproliferative activity against human gastric cancer (MKN-45) cell line and its biocompatibility effect on normal cells using human dermal fibroblast (HDF) cell line. Average molecular weight and monosaccharide composition were determined by high-pressure size exclusion chromatography (HPSEC) with multi-angle laser light scattering (MALLS) and high-pressure anion exchange chromatography (HPAEC), respectively. Fourier transform infrared (FTIR) spectroscopy was used for the partial characterization of the EPS. The EPS effect on the cell proliferation and viability of MKN-45 and HDF cells was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and trypan blue dye exclusion, respectively. Strain TBZ112 excreted 480 mg.l-1 of the EPS under optimal growth conditions. The EPS had a molecular weight of 5.052 kDa and was a heteropolysaccharide containing ten moieties mainly composed of mannose (19.95%), glucosamine (15.55%), galacturonic acid (15.43%), arabinose (12.24%), and glucuronic acid (12.05%). No significant difference of the EPS treatments on the proliferation activity of MKN-45 and HDF cells were observed (P > 0.05). For the first time, the EPS from Halorubrum sp. TBZ112, an extremely halophilic archaeon related to Halorubrum genus, was isolated and chemically characterized. The EPS from Halorubrum sp. TBZ112 possesses a relatively low molecular weight and might be applied as a biocompatible compound. More investigations are needed to determine other biological activities of the EPS along with further details of its chemical structure.
exopolysaccharide (EPS), Antiproliferative effect, Halorubrum sp.TBZ112, Monosaccharide composition
NCBI PubMed ID: 30555767Publication DOI: 10.1007/s13205-018-1515-5Journal NLM ID: 101565857Publisher: Berlin: Springer
Correspondence: Korosh Khanaki
;
Institutions: Medical Biotechnology Research Center, School of Paramedicine, Guilan University of Medical Sciences, Rasht, Iran, Institut Pascal UMR CNRS 6602, Université Clermont Auvergne, F-63000 Clermont-Ferrand, France, EA3900 BIOPI, Université de Picardie Jules Verne, Avenue des facultés, Le Bailly, 80025 Amiens cedex, France
Methods: HPAEC, FTIR, composition analysis, HPSEC-MALLS, extraction, statistical analysis
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7. Compound ID: 3019
|
S-3)-+
|
-4)-b-D-GlcpNAcA-(1-1)-Subst-(4-4)-b-D-GlcpNAcA-(1-
Subst = 2-(1,2-dihydroxy-ethoxy)-D-glycerol = SMILES O{1}CC(CO)O{4}C(O)CO |
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Structure type: polymer chemical repeating unit
Compound class: EPS
The structure is contained in the following publication(s):
- Article ID: 1083
Parolis H, Parolis LAS, Boán IF, Rodríguez-Valera F, Widmalm G, Manca MC, Jansson P, Sutherland IW "The structure of the exopolysaccharide produced by the halophilic Archaeon Haloferax mediterranei strain R4 (ATCC33500)" -
Carbohydrate Research 295 (1996) 147-156
The halophilic Archaeon Haloferax mediterranei exudes into the growth medium a high molecular weight sulfated polysaccharide. The structure of the repeating unit of this polymer was determined by a combination of glycose, methylation, and sulfate analysis, periodate oxidation, and 1D and 2D NMR spectroscopic analysis of the native and periodate-oxidised/reduced polysaccharides. The location of the sulfate group was established from the 1H and 13C NMR data. The structure of the repeating unit of the polysaccharide may be written as [formula: see text]
structure, strain, exopolysaccharide, sulfate, Archaeon, Haloferax, halophilic
NCBI PubMed ID: 9002190Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, School of Pharmaceutical Sciences, Rhodes University, Grahamstown, 6140, South Africa, Departamento de Genetica y Microbiologia, Universidad de Alicante, Campus de San Juan, Apdo. 374, E-03080 Alicante, Spain, Clinical Research centre, Analytical Unit, Karolinska Institute, Huddinge Hospital, Huddinge, Sweden, Institute of Cell and Molecular Biology, Edingurgh University, Mayfield Rd. Edingurgh, EH9 3JH, UK
Methods: methylation, periodate oxidation, NMR-2D, NMR, sugar analysis, sulfate analysis
- Article ID: 5253
Vijayendra SV, Shamala TR "Film forming microbial biopolymers for commercial applications-A review" -
Critical Reviews in Biotechnology 34(4) (2014) 338-357
Microorganisms synthesize intracellular, structural and extracellular polymers also referred to as biopolymers for their function and survival. These biopolymers play specific roles as energy reserve materials, protective agents, aid in cell functioning, the establishment of symbiosis, osmotic adaptation and support the microbial genera to function, adapt, multiply and survive efficiently under changing environmental conditions. Viscosifying, gelling and film forming properties of these have been exploited for specific significant applications in food and allied industries. Intensive research activities and recent achievements in relevant and important research fields of global interest regarding film forming microbial biopolymers is the subject of this review. Microbial polymers such as pullulan, kefiran, bacterial cellulose (BC), gellan and levan are placed under the category of exopolysaccharides (EPS) and have several other functional properties including film formation, which can be used for various applications in food and allied industries. In addition to EPS, innumerable bacterial genera are found to synthesis carbon energy reserves in their cells known as polyhydroxyalkanoates (PHAs), microbial polyesters, which can be extruded into films with excellent moisture and oxygen barrier properties. Blow moldable biopolymers like PHA along with polylactic acid (PLA) synthesized chemically in vitro using lactic acid (LA), which is produced by LA bacteria through fermentation, are projected as biodegradable polymers of the future for packaging applications. Designing and creating of new property based on requirements through controlled synthesis can lead to improvement in properties of existing polysaccharides and create novel biopolymers of great commercial interest and value for wider applications. Incorporation of antimicrobials such as bacteriocins or silver and copper nanoparticles can enhance the functionality of polymer films especially in food packaging applications either in the form of coatings or wrappings. Use of EPS in combinations to obtain desired properties can be evaluated to increase the application range. Controlled release of active compounds, bioactive protection and resistance to water can be investigated while developing new technologies to improve the film properties of active packaging and coatings. An holistic approach may be adopted in developing an economical and biodegradable packaging material with acceptable properties. An interdisciplinary approach with new innovations can lead to the development of new composites of these biopolymers to enhance the application range. This current review focuses on linking and consolidation of recent research activities on the production and applications of film forming microbial polymers like EPS, PHA and PLA for commercial applications. © 2014 Informa Healthcare USA, Inc.
exopolysaccharides, fermentation, antimicrobial films, biodegradable, polyhydroxyalkanoates, polylactic acid
NCBI PubMed ID: 23919238Publication DOI: 10.3109/07388551.2013.798254Journal NLM ID: 8505177Publisher: CRC Press
Correspondence: Vijayendra SV
; Vijayendra SV
Institutions: Food Microbiology Department, CSIR-Central Food Technological Research Institute (A constituent laboratory of Council of Scientific and Industrial Research, New Delhi), Mysore, Karnataka, India
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8. Compound ID: 6022
|
D-Rhap2Me-(1-2)-+
|
D-Manp2Me-(1-4)-D-GlcpNAcA-(1-4)-D-GlcpA-(1-4)-D-Glcp-(1-4)-D-GlcpA2Me-(1-4)-D-Manp-(1-3)-Ser |
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Structure type: oligomer
Compound class: O-glycoprotein
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_137485,IEDB_1394181,IEDB_140630,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_150900,IEDB_152206,IEDB_423153,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2679
Reinhold BB, Hauer CR, Plummer TH, Reinhold VN "Detailed structural analysis of a novel, specific O-linked glycan from the prokaryote Flavobacterium meningosepticum" -
Journal of Biological Chemistry 270 (1995) 13197-13203
Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
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9. Compound ID: 8142
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
- Article ID: 3825
Brooks BW, Lutze-Wallace CL, MacLean LL, Vinogradov E, Perry MB "Identification and differentiation of Taylorella equigenitalis and Taylorella asinigenitalis by lipopolysaccharide O-antigen serology using monoclonal antibodies" -
Canadian Journal of Veterinary Research 74(1) (2010) 18-24
Lipopolysaccharides (LPSs) from Taylorella equigenitalis, the causative agent of contagious equine metritis, and T. asinigenitalis were compared by sodium dodecyl sulphate-polyacrylamide gel electrophoresis (SDS-PAGE). Lipopolysaccharide profiles of 11 T. equigenitalis strains were similar, but different from the profiles of 3 T. asinigenitalis strains, and the profiles of 2 T. asinigenitalis strains were similar to each other. The serological specificities of the LPSs from these 14 strains were examined by immunoblotting and enzyme-linked immunosorbent assay with monoclonal antibodies (MAbs) to the LPSs of the T. equigenitalis and T. asinigenitalis type strains and T. asinigenitalis strain 2329-98. A MAb to T. equigenitalis LPS O-polysaccharide (O-PS) (M2560) reacted with LPSs from all T. equigenitalis strains but did not react with LPSs from the 3 T. asinigenitalis strains or with 43 non-Taylorella bacteria. Three MAbs to the T. asinigenitalis type strain LPS O-PS or core epitopes (M2974, M2982, M3000) reacted with the homologous strain and T. asinigenitalis strain Bd 3751/05, but not with any of the other bacteria. Five MAbs to T. asinigenitalis 2329-98 LPS O-PS or core epitopes (M2904, M2907, M2910, M2923, M2929) reacted only with this strain. Proton nuclear magnetic resonance spectra of the O-PSs of the type strains of T. equigenitalis and T. asinigenitalis provided fingerprint identification and differentiation of these 2 organisms. The serological results were consistent with our previous finding that the O-antigen of the type strain of T. equigenitalis, being a linear polymer of disaccharide repeating [→4)-α-L-GulpNAc3NAcA-(1→4)-β-D-ManpNAc3NAcA-(1→] units, differs from that of the T. asinigenitalis O-antigen polymer that is composed of repeating [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→] units. Lipopolysaccharide O-PS could be a specific marker for identification and differentiation of T. equigenitalis and T. asinigenitalis, and provide the basis for the development of specific detection assays for T. equigenitalis.
Lipopolysaccharide, O-antigen, monoclonal antibodies, serology, differentiation, veterinary, Taylorella equigenitalis
NCBI PubMed ID: 20357953Journal NLM ID: 8607793Publisher: Canadian Veterinary Medical Association
Correspondence: brian.brooks@inspection.gc.ca
Institutions: Canadian Food Inspection Agency, Ottawa Laboratory (Fallowfield), Ottawa, Ontario K2H 8P9 (Brooks, Lutze-Wallace), National Research Council of Canada, Institute of Biological Sciences, Ottawa, Ontario K1A 0R6 (MacLean, Vinogradov, Perry).
Methods: 1H NMR, SDS-PAGE, ELISA, serological methods, immunoblotting
- Article ID: 5157
Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Streptococcus suis serotype 3 and serotype 18 capsular polysaccharides contain di-N-acetyl-bacillosamine" -
Carbohydrate Research 466 (2018) 18-29
Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n. To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report. This led to the identification of homologues of UDP-QuiNAc4NAc synthesis genes in S. suis serotype 18. Thus, the repeating unit sequence for serotype 18 is: [3)d-GalNAc(α1-3)[d-Glc (β1-2)]d-GalA4OAc(β1-3)d-GalNAc(α1-3)d-QuiNAc4NAc(α1-]n. A correlation between S. suis serotypes 3 and 18 CPS sequences and genes of these serotypes' cps loci encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotypes 3 and 18.
polysaccharide, capsular polysaccharide, polysaccharides, carbohydrate structure, Streptococcus suis, Di-N-Acetyl-bacillosamine, Serotype 18, Serotype 3
NCBI PubMed ID: 30014879Publication DOI: 10.1016/j.carres.2018.07.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mariela.segura@umontreal.ca
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
Methods: 13C NMR, 1H NMR, periodate oxidation, gel filtration, NMR-2D, GC-MS, de-O-acylation, sugar analysis, methanolysis, SEC-MALS, bioinformatic analysis
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10. Compound ID: 8143
Structure type: fragment of a bigger structure
Aglycon: (1->3) O-polysaccharide
Compound class: O-polysaccharide
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
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11. Compound ID: 8144
Structure type: oligomer
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
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12. Compound ID: 8145
Structure type: oligomer
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
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13. Compound ID: 8146
|
Subst-(1-1:3-2)-+
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b-D-GlcpNAmA-(1-3)-a-D-QuipN4NAc
Subst = 2-metyl-oxazoline = SMILES {3}N={1}C(C)O |
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Structure type: oligomer
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
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14. Compound ID: 8147
|
b-D-GlcpNAmA-(1-3)-b-D-QuipNAc4NAc-(1-3)-b-D-GlcpNAmA-(1-3)-b-D-QuipNAc4NAc-(1-2)-D-gro-D-manHepp-(1-2)-D-gro-D-manHepp-(1-3)-D-gro-D-manHepp-(1-?)-Kdo |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_2189046
The structure is contained in the following publication(s):
- Article ID: 3563
Vinogradov E, MacLean LL, Brooks BW, Lutze-Wallace C, Perry MB "Structure of the O-polysaccharide of the lipopolysaccharide produced by Taylorella asinigenitalis type strain (ATCC 700933)" -
Biochemistry and Cell Biology 86(3) (2008) 278-284
Taylorella asinigenitalis sp. nov is a nonpathogenic gram-negative bacterium recently isolated from the genital tract of male donkeys. The bacterium is phenotypically indistinguishable from Taylorella equigenitalis, a pathogen that is the cause of contagious equine metritis, a highly communicable venereal disease of horses. The structural analysis of the lipopolysaccharide produced by T. asinigenitalis sp. nov (ATCC 700933) demonstrated that its O-polysaccharide (O-PS) component is a linear unbranched polymer of repeating disaccharide units composed of 1,3-linked pyranosyl residues of 2,4-diacetamido-2,4-dideoxy-β-D-quinovose (bacillosamine) and 2-acetamidino-2-deoxy-β-D-glucuronic acid, and has the structure [→3)-β-D-QuipNAc4NAc-(1→3)-β-D-GlcpNAmA-(1→]n. The chemical structure and serological characteristics of the T. asinigenitalis O-PS are distinct from those of the O-PS of the T. equigenitalis type strain, thus providing a cell-surface target macromolecule that can be used to distinguish pathogenic from nonpathogenic Taylorella sp. clinical isolates.
Lipopolysaccharide, structure, O-polysaccharide, Taylorella asinigenitalis
NCBI PubMed ID: 18523489Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, chemical methods, NMR-1D, CE-MS
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15. Compound ID: 8648
|
a-D-Glcp-(1-4)-+
|
-2)-a-L-Rhap3(60%)Ac4(25%)Ac-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAcA6(60%)Ac-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3759
Perepelov AV, L'vov VL, Liu B, Senchenkova SN, Shekht ME, Shashkov AS, Feng L, Aparin PG, Wang L, Knirel YA "A similarity in the O-acetylation pattern of the O-antigens of Shigella flexneri types 1a, 1b and 2a" -
Carbohydrate Research 344(5) (2009) 687-692
Shigella flexneri type 2a is the first, and type 1b is the second, most prevalent isolates from patients with shigellosis in Russia. The O-specific polysaccharides (OPSs, O-antigens) of S. flexneri types 1-5 possess a common →2)-α-L-RhapIII-(1→2)-α-L-RhapII-(1→3)-α-L-RhapI-(1→3)-β-D-GlcpNAc-(1→ backbone and differ from each other in its glucosylation or/and O-acetylation at various positions, the modifications being responsible for various O-factors. It was suggested that O-factor 6 expressed by type 1b is associated with O-acetylation of RhaI at position 2 but more than one O-acetyl group has been detected in the type 1b OPS [Kenne, L. et al. Eur. J. Biochem.1978, 91, 279-284]. In this work, O-acetylation of RhapI in the type 1b OPS was confirmed by NMR spectroscopy and location of an additional O-acetyl group at position either 3 (major) or 4 (minor) of RhapIII was determined. Type 1a differs from type 1b in the lack of O-acetylation of RhapI only. In type 2a, in addition to two reported major O-acetyl groups at position 6 of GlcNAc and position 3 of RhapIII [Kubler-Kielb, J. et al. Carbohydr. Res.2007, 342, 643-647], a minor O-acetyl group was found at position 4 of RhaIII. Therefore, RhapIII is O-acetylated in the same manner in all three S. flexneri serotypes studied.
O-antigen, Shigella flexneri, O-specific polysaccharide, O-acetylation, bacterial polysaccharide structure
NCBI PubMed ID: 19246033Publication DOI: 10.1016/j.carres.2009.01.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, de-O-acetylation, acid degradation
- Article ID: 5188
Micoli F, Costantino P, Adamo R "Potential targets for next generation anti-microbial glycoconjugate vaccines" -
FEMS Microbiology Reviews 42(3) (2018) 388-423
Cell surface carbohydrates have been proven optimal targets for vaccine development. Conjugation of polysaccharides to a carrier protein triggers a T-cell dependent immune response to the glycan moiety. Licensed glycoconjugate vaccines are produced by chemical conjugation of capsular polysaccharides to prevent meningitis caused by meningococcus, pneumococcus and Haemophilus influenzae type b. However, other classes of carbohydrates (O-antigens, exopolysaccharides, wall/teichoic acids) represent attractive targets for developing vaccines.Recent analysis from WHO/CHO underpins alarming concern towards antibiotic resistant bacteria, such as the so called ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter spp.) and additional pathogens such as Clostridium difficile and Group A Streptococcus. Fungal infections are also becoming increasingly invasive for immunocompromised patients or hospitalized individuals. Other emergencies could derive from bacteria which spread during environmental calamities (Vibrio cholerae) or with potential as bioterrorism weapons (Burkholderia pseudomallei and mallei, Francisella tularensis). Vaccination could aid reducing the use of broad spectrum antibiotics and provide protection by herd immunity also to individuals who are not vaccinated.This review analyses structural and functional differences of the polysaccharides exposed on the surface of emerging pathogenic bacteria, combined with medical need and technological feasibility of corresponding glycoconjugate vaccines.
carbohydrates, glycoconjugates, vaccines, glycoengineering, antimicrobial resistance
NCBI PubMed ID: 29547971Publication DOI: 10.1093/femsre/fuy011Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: Roberto Adamo
Institutions: GSK Vaccines Institute for Global Health (GVGH), Via Fiorentina 1, 53100 Siena
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