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1. Compound ID: 6
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Pyr-(2-6:2-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1-4)-+
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-3)-a-D-Galp-(1-6)-b-D-Galp-(1-3)-b-D-Gal-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: amylovoran
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_423153,IEDB_742248,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3
Bernhard F, Schullerus D, Bellemann P, Nimtz M, Coplin DL, Geider K "Genetic transfer of amylovoran and stewartan synthesis between Erwinia amylovora and Erwinia stewartii" -
Microbiology 142 (1996) 1087-1096
DNA fragments with ams genes of Erwinia amylovora and cps genes of Erwinia stewartii were transferred to exopolysaccharide (EPS)-deficient mutants of the other species. The resulting EPSs were characterized by sensitivity to EPS-dependent bacteriophages, staining with amylovoran-specific fluorescein-isothiocyanate-labelled lectin and chemical techniques, such as determination of the sugar composition and methylation analysis in order to distinguish between amylovoran and stewartan. Degradation by the stewartan-dependent phage phi-K9 was used to detect stewartan production, and staining with a lectin from Abrus precatorius detected amylovoran capsules. The patterns of sugar linkages were determined by methylation analysis. Stewartan contained a significantly higher glucose to galactose ratio than amylovoran and produced a characteristic signal from 6-linked glucose residues. By these criteria, most E. stewartii cps mutants displayed exclusively amylovoran synthesis when complemented with the E. stewartii cps genes produced stewartan. The complementation to an EPS-positive phenotype may require most genes of the ams or the cps operon. An exception was an E. stewartii cpsK mutant that made predominantly stewartan when complemented with the ams cosmid. IR spectra showed that both amylovoran and stewartan were acylated when synthetized in E. amylovora, but not in E. stewartii. The amylovoran-producing E. stewartii merodiploids regained virulence to corn seedlings when mucoidy was restored by the ams cluster, but the stewartan-producing E. amylovora ams-/cps+ strains were weakly virulent on pear slices and avirulent on apple seedlings.
amylovoran, biosynthesis, complementation, Erwinia, Erwinia amylovora, fireblight, genetic, Stewart's wilt, stewartan, synthesis, transfer, transgenic bacteria
NCBI PubMed ID: 8704950Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Max-Planc-Institut fur medicinische Forschung, Jahnshtrasse 29, D-69120, Heidelberg, Germany
Methods: methylation, IR, virulence assays
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2. Compound ID: 411
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R-Pyr-(2-6:2-4)-a-D-Galp-(1-2)-+
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-3)-a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_158539,IEDB_189517,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 141
Van Calsteren MR, Pau-Roblot C, Begin A, Roy D "Structure determination of the exopolysaccharide produced by Lactobacillus rhamnosus strains RW-9595M and R" -
Biochemical Journal (2002) 7-17
Exopolysaccharides (EPSs) were isolated and purified from Lactobacillus rhamnosus strains RW-9595M, which has been shown to possess cytokine-stimulating activity, and R grown under various fermentation conditions (carbon source, incubation temperature and duration). Identical (1)H NMR spectra were obtained in all cases. Molecular masses were determined by gel permeation chromatography. The primary structure was elucidated using chemical and spectroscopic techniques. Organic acid, monosaccharide and absolute configuration analyses gave the following composition: pyruvate, 1; D-glucose, 2; D-galactose, 1; and l-rhamnose, 4. Methylation analysis indicated the presence of three residues of 3-linked rhamnose, and one residue each of 2,3-linked rhamnose, 2-linked glucose, 3-linked glucose and 4,6-linked galactose. The EPS was submitted to periodate oxidation followed by borohydride reduction. Monosaccharide analysis of the resulting polysaccharide gave the new composition: rhamnose, 4; and glucose, 1. Methylation analysis confirmed the loss of the 2-linked glucose and 4,6-linked galactose residues. On the basis of one- and two-dimensional (1)H and (13)C NMR data, the structure of the native EPS was consistent with the following heptasaccharide repeating unit: {3Rhaα-3Glcβ-3[Gal4,6(R)Pyα- 2]Rhaα-3Rhaα-3Rhaα-2Glcα-}(n) where Rha corresponds to rhamnose (6-deoxymannose) and Py corresponds to pyruvate acetal. Complete (1)H and (13)C assignments are reported for the native and the corresponding pyruvate-hydrolysed polysaccharide. Electrospray MS and MS/MS data are given for the oligosaccharide produced by Smith degradation.
NMR, Lactic acid bacteria, sequence, heptasaccharide repeating unit, pyruvate substituent
NCBI PubMed ID: 11903041Publication DOI: 10.1016/S0008-6215(99)00181-0Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Correspondence: vancalsteren@em.agr.ca
Institutions: Centre de recherche et de developpement sur les aliments, Agriculture et Agroalimentaire Canada, 3600 boulevard Casavant Ouest, Saint- Hyacinthe, Quebec, Canada J2S 8E3
Methods: NMR-2D, methylation, NMR, mild acid hydrolysis, Smith degradation
- Article ID: 5067
Birch J, Harðarson HK, Khan S, Van Calsteren MR, Ipsen R, Garrigues C, Almdal K, Hachem MA, Svensson B "Effect of repeat unit structure and molecular mass of lactic acid bacteria hetero-exopolysaccharides on binding to milk proteins" -
Carbohydrate Polymers 177 (2017) 406-414
Interactions of exopolysaccharides and proteins are of great importance in food science, but complicated to analyze and quantify at the molecular level. A surface plasmon resonance procedure was established to characterize binding of seven structure-determined, branched hetero-exopolysaccharides (HePSs) of 0.14-4.9MDa from lactic acid bacteria to different milk proteins (β-casein, κ-casein, native and heat-treated β-lactoglobulin) at pH 4.0-5.0. Maximum binding capacity (RUmax) and apparent affinity (KA,app) were HePS- and protein-dependent and varied for example 10- and 600-fold, respectively, in the complexation with native β-lactoglobulin at pH 4.0. Highest RUmax and KA,app were obtained with heat-treated β-lactoglobulin and β-casein, respectively. Overall, RUmax and KA,app decreased 6- and 20-fold, respectively, with increasing pH from 4.0 to 5.0. KA,app was influenced by ionic strength and temperature, indicating that polar interactions stabilize HePS-protein complexes. HePS size as well as oligosaccharide repeat structure, conferring chain flexibility and hydrogen bonding potential, influence the KA,app.
Binding parameters, Dynamic light scattering (DLS), Hetero-exopolysaccharides (HePSs), Surface plasmon resonance (SPR), β- and κ-casein, β-lactoglobulin
NCBI PubMed ID: 28962786Publication DOI: 10.1016/j.carbpol.2017.08.055Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: B. Svensson
Institutions: Enzyme and Protein Chemistry, Department of Biotechnology and Biomedicine, Technical University of Denmark, Elektrovej, building 375, DK-2800 Kgs. Lyngby, Denmark, Department of Micro- and Nanotechnology, Technical University of Denmark, Produktionstorvet, building 423, DK-2800 Kgs. Lyngby, Denmark, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, 3600 Casavant Boulevard West, Saint-Hyacinthe, Quebec J2S 8E3, Canada, Department of Food Science, University of Copenhagen, Rolighedsvej 26, DK-1958 Frederiksberg C, Denmark, CED-Discovery, Chr Hansen A/S, DK-2970 Hørsholm, Denmark
Methods: gel filtration, 13C NMR, 1H NMR, sugar analysis, ESI-MS, acid hydrolysis, GC, MS/MS, methanolysis, reduction with NaBD4, acetylation, SPR, protein immobilization, dynamic light scattering
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 5880
De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
carbohydrates, polysaccharides, Lactic acid bacteria, exopolysaccharides, glycolipids, glycoproteins, Glycomics
Publication DOI: 10.1016/B978-044451967-2/00129-XPublisher: Elsevier
Correspondence: ldvuyst@vub.ac.be
Editors: Barchi J, Kamerling H
Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
- 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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3. Compound ID: 945
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 286
Keller M, Roxlau A, Weng WM, Schmidt M, Quandt J, Niehaus K, Jording D, Arnold W, Puhler A "Molecular analysis of the Rhizobium meliloti mucR gene regulating the biosynthesis of the exopolysaccharides succinoglycan and galactoglucan" -
Molecular Plant-Microbe Interactions 8 (1995) 267-277
The Rhizobium meliloti Tn5 mutant Rm3131, producing galactoglucan (EPS II) instead of succinoglycan (EPS I), was complemented by a 3.6-kb EcoRI-fragment of the Rhizobium meliloti genome. Sequencing of this fragment revealed six open reading frames (ORFs). The ORF found to be affected in the mutant Rm3131 codes for a putative protein of 15.7 kDa and forms a monocistronic transcriptional unit. Further genetic analysis revealed that the gene mutated in Rm3131 is identical to the previously described R. meliloti mucR gene (H. Zhan, S.B. Levery, C. C. Lee, and J.A. Leigh, 1989, Proc. Natl. Acad. Sci. USA 86:3055-3059). By hybridization it was shown that a mucR homologous gene is present in several rhizobacteria. The deduced amino acid sequence of MucR showed nearly 80% identity to the Agrobacterium tumefaciens Ros protein, a negative regulator of vir genes and necessary for succinoglycan production. MucR contains like Ros a putative zinc finger sequence of the C2H2 type. Transcriptional fusions of genes for EPS I and EPS II synthesis, the so-called exo and exp genes, with the marker gene lacZ were used to delineate the role of mucR for exo and exp gene expression. It was found that exp genes are negatively regulated by MucR on the transcriptional level, whereas a posttranscriptional regulation by MucR is assumed for exo genes. Furthermore, mucR is negatively regulating its own transcription.
symbiosis, exopolysaccharide synthesis, gene regulation
NCBI PubMed ID: 7756693Publication DOI: 10.1094/MPMI-8-0267Journal NLM ID: 9107902Institutions: Lehrstuhl für Genetik, Fakultät für Biologie, Universität Bielefeld, Federal Republic of Germany
Methods: 13C NMR, DNA sequencing, DNA techniques, genetic methods, enzyme assay
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4. Compound ID: 1295
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 404
Vinion-Dubiel AD, Goldberg JB "Lipopolysaccharide of Burkholderia cepacia complex" -
Journal of Endotoxin Research 9(4) (2003) 201-213
Burkholderia cepacia complex (Bcc) is a group of phenotypically similar, genetically distinct bacteria that are beneficial to the environment but can also cause severe human infections. Bcc are being exploited for use as bioremediation agents and as a way to combat agricultural plant diseases. However, Bcc can cause lung infections in patients with chronic granulomatous disease or cystic fibrosis often resulting in mortality of these patients. Since it is unclear what bacterial components are necessary for causing human infections, studies of Bcc have focused on identifying putative virulence factors. As in other Gram-negative bacteria, the lipopolysaccharide (LPS) of Bcc induces a strong immune response that can contribute to host cell damage. The unusual structure of Bcc LPS lowers the anionic charge of the Bcc cell surface, which inhibits the binding and subsequent effects of cationic antibiotics. These distinguishing features include the substitution of a Ko for a Kdo residue in the inner core oligosaccharide and Ara4N residues bound to phosphates of the lipid A backbone. The structures of O antigen subunits and the consequent serotypes will also be discussed, with particular reference to the O antigen biosynthetic loci of two Bcc strains.
Lipopolysaccharide, structure, Burkholderia, Burkholderia cepacia, O-antigen, complex, endotoxin, Re
NCBI PubMed ID: 12935351Publication DOI: 10.1177/09680519030090040101Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Microbiology, University of Virginia Health Sciences Center, Charlottesville, VA 22908-0734, USA
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5. Compound ID: 1347
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b-D-Glcp-(1-4)-+
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Pyr-(2-6:2-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1-3)-a-D-Galp-(1-3)-L-Fuc |
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Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_7,SB_86
The structure is contained in the following publication(s):
- Article ID: 426
Yang BY, Montgomery R "b-Elimination of glucosyluronic residues during methylation of an acidic polysaccharide from Erwinia chrysanthemi CU 643" -
Carbohydrate Research 332(3) (2001) 317-323
The Erwinia chrysanthemi CU643 EPS has a linear hexasaccharide repeating unit in which a 4-linked uronic acid residue is present. The EPS was methylated by either the NaOH-Me2SO-MeI or Li-dimsyl procedure. MALDI-TOF MS analysis of the methylated products indicates that the beta-eliminative degradation occurs during the methylation, as characterized by serial fragments of the hexasaccharide repeating units. The degradation was clearly defined from the methylation of a glucosyluronic-containing pyruvated pentasaccharide
methylation, acidic extracellular polysaccharide, Erwinia chrysanthemi, β-elimination
NCBI PubMed ID: 11376611Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City, Iowa, IA 52242, USA
Methods: methylation, GLC-MS, MALDI-TOF MS
- Article ID: 1293
Yang BY, Brand J, Montgomery R "Pyruvated galactose and oligosaccharides from Erwinia chrysanthemi Ech6 extracellular polysaccharide" -
Carbohydrate Research 331(1) (2001) 59-67
The acidic extracellular polysaccharide of Ech6 was depolymerized by fuming HCl. The pyruvated sugars were isolated and characterized by methods that included a combination of low-pressure gel-filtration and high-pH anion-exchange chromatographies, methylation linkage analyses, mass (GC-MS and MALDI-TOF MS) and 1H NMR (1D and 2D) spectroscopies. The following pyruvated sugars were obtained: 4,6-O-(1-carboxyethylidene)-D-Galp; 4,6-O-(1-carboxyethylidene)-α-D-Galp-(1→4)-β-D-GlcAp-(1→3)-D-Galp; 4,6-O-(1-carboxyethylidene)-α-D-Galp-(1→4)-α-D-GlcAp-(1→3)-α-D-Galp-(1→3)-L-Fucp; 4,6-O-(1-carboxyethylidene)-α-D-Galp-(1→4)-β-D-GlcAp-(1→3)-α-D-Galp-(1→3)-L-[β-D-Glcp-(1→4)]-Fucp. These oligosaccharides present potential haptenes for the development of specific antibodies and confirm the partial structure proposed previously for the extracellular polysaccharide from Erwinia chrysanthemi Ech6 [Yang, B. Y.; Gray, J. S. S.; Montgomery, R. Int. J. Biol. Macromol., 1994, 16, 306-312].
structure, extracellular polysaccharide, Erwinia chrysanthemi, Pyruvated sugars
NCBI PubMed ID: 11284505Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City 52242, USA
Methods: NMR-2D, methylation, partial acid hydrolysis, NMR, MALDI-TOF MS
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6. Compound ID: 1595
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R-Pyr-(2-6:2-4)-+
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-3)-b-D-GlcpNAc-(1-2)-a-D-Galp-(1-4)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130651,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_144987,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_742247,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_31,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 494
Perepelov AV, Rozalski A, Bartodziejska B, Senchenkova SN, Knirel YA "Structure of the O-polysaccharide of Proteus mirabilis O19 and reclassification of certain Proteus strains that were formerly classified in serogroup O19" -
Archivum Immunologiae et Therapiae Experimentalis 52(3) (2004) 188-196
INTRODUCTION: Bacteria of the genus Proteus are a common cause of urinary tract infections. The O-polysaccharide chain of their LPS (O-antigen) defines the serological specificity of these bacteria. Based on the immunospecificity of the O-antigens, two species, P. mirabilis and P. vulgaris, were classified into 49 O-serogroups, and more O-serogroups for strains of these species and P. penneri have been subsequently proposed. MATERIAL AND METHODS: The lipopolysaccharide of P.mirabilis CCUG 19011 from serogroup O19 was degraded under mildly acidic and mildly alkaline conditions. Polysaccharides thus obtained were studied by chemical methods, including O -deacetylation, sugar and methylation analyses, and 1H- and 13C NMR spectroscopy. Antisera were obtained by immunization of New Zealand white rabbits with heat-killed bacteria. In serological studies, enzyme immunosorbent assay, passive hemolysis test, and inhibition of passive hemolysis were used. RESULTS: The following structure of the O-polysaccharide repeating unit was established: →3)-β-D-GlcpNAc-(1→3)-α-D-GalpNAc4,6(R-Pyr)-(1→4)-a-D-GalpA-(1→3)α-L-Rhap2Ac-(1→ where R-Pyr is (R)-1-carboxyethylidene (an acetal-linked pyruvic acid). This structure is significantly different from the O-polysaccharide structures of P. vulgaris, P.hauseri and P. penneri strains from the same Proteus serogroup O19. CONCLUSIONS: Based on immunochemical studies of the lipopolysaccharides, it is suggested 1) to keep P. vulgaris CCUG 4654 and P. penneri 31 in serogroup O19 as two subgroups, 2) to reclassify P. mirabilis CCUG 19011 into a new Proteus serogroup, O51, and 3) to classify serologically related strains, including P. vulgaris ATCC 49990, P. hauseri> 1732-80 and 1086-80, P. penneri 15, and some other P. penneri strains, in yet another Proteus serogroup, O52.
Lipopolysaccharide, structure, O-polysaccharide, Proteus mirabilis, serological classification, pyruvic acid
NCBI PubMed ID: 15247885Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Methods: NMR-2D, methylation, NMR
- Article ID: 1341
Zych K, Kowalczyk M, Toukach FV, Paramonov NA, Shashkov AS, Knirel YA, Sidorczyk Z "Structural and immunochemical studies of O-specific polysaccharide of Proteus penneri strain 15" -
Archivum Immunologiae et Therapiae Experimentalis 45 (1997) 435-441
On the basis of sugar analysis and 1H- and 13C NMR spectroscopy, it was shown that the O-specific polysaccharide of Proteus penneri strain 15 has a trisaccharide repeating unit, including an acetal-linked pyruvic acid residue, and is structurally identical to the capsular polysaccharide of Proteus vulgaris strain ATCC49990. Serological studies supported this conclusion and demonstrated the presence in the homological antiserum of both anti-core and anti-O chain antibodies reacting with a lipopolysaccharide (LPS) epitope containing N-acetylglucosamine and galactose residues
Lipopolysaccharide, LPS, structure, strain, structural, characterization, polysaccharide, acid, O-specific, O-specific polysaccharide, Proteus, serology, Proteus penneri, immunochemical, pyruvic acid, acetal
NCBI PubMed ID: 9437499Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Institutions: Institute of Microbiology and Immunology, University of Lodz, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis
- Article ID: 1466
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 2289
Perry MB, MacLean LL "The structure of the polysaccharide produced by Proteus vulgaris (ATCC 49990)" -
Carbohydrate Research 253 (1994) 257-263
Journal NLM ID: 0043535Publisher: Elsevier
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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7. Compound ID: 1840
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_742246,IEDB_918313,SB_7,SB_87
The structure is contained in the following publication(s):
- Article ID: 579
D'Haeze W, Glushka J, De Rycke R, Holsters M, Carlson RW "Structural characterization of extracellular polysaccharides of Azorhizobium caulinodans and importance for nodule initiation on Sesbania rostrata" -
Molecular Microbiology 52(2) (2004) 485-500
Summary During lateral root base nodulation, the microsymbiont Azorhizobium caulinodans enters its host plant, Sesbania rostrata, via the formation of outer cortical infection pockets, a process that is characterized by a massive production of H(2)O(2). Infection threads guide bacteria from infection pockets towards nodule primordia. Previously, two mutants were constructed that produce lipopolysaccharides (LPSs) similar to one another but different from the wild-type LPS, and that are affected in extracellular polysaccharide (EPS) production. Mutant ORS571-X15 was blocked at the infection pocket stage and unable to produce EPS. The other mutant, ORS571-oac2, was impaired in the release from infection threads and was surrounded by a thin layer of EPS in comparison to the wild-type strain that produced massive amounts of EPS. Structural characterization revealed that EPS purified from cultured and nodule bacteria was a linear homopolysaccharide of α-1,3-linked 4,6-O-(1-carboxyethylidene)-d-galactosyl residues. In situ H(2)O(2) localization demonstrated that increased EPS production during early stages of invasion prevented the incorporation of H(2)O(2) inside the bacteria, suggesting a role for EPS in protecting the microsymbiont against H(2)O(2). In addition, ex planta assays confirmed a positive correlation between increased EPS production and enhanced protection against H(2)O(2).
extracellular polysaccharide, EPS, Azorhizobium, Azorhizobium caulinodans, EPS production
NCBI PubMed ID: 15066035Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: wim@ccrc.uga.edu
Institutions: Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Road, Athens, GA 30602-4712, USA
Methods: 13C NMR, 1H NMR, GLC-MS, PAGE
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8. Compound ID: 2017
|
R-Pyr-(2-6:2-4)-a-D-Galp-(1-3)-+
|
-3)-a-D-Manp-(1-3)-b-D-Galp-(1-2)-a-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 619
Aucken HM, Wilkinson SG, Pitt TL "Re-evaluation of the serotypes of Serratia marcescens and separation into two schemes based on lipopolysaccharide (O) and capsular polysaccharide (K) antigens" -
Microbiology 144 (1998) 639-653
Chemical and serological analysis has revealed that many of the 29 O serotype reference strains of Serratia marcescens contain both neutral and acidic polysaccharides which correspond to LPS O antigens and capsular K antigens, respectively. New O and K antigen typing schemes have therefore been devised, based on the known chemical structures of the surface polysaccharides of the organism. These schemes were designed to allow the specific detection of these antigens on unknown strains using ELISAs. O antigens were detected using whole cells cultured in broth then autoclaved to remove capsular material, while K antigens were detected using formolized whole cells which had been cultured on glycerol agar to enhance capsule production. After testing with the 29 reference strains as well as 423 distinct clinical strains, it was apparent that different aspects of chemical structure were associated with different degrees of serological reactivity and the typing schemes were modified further to accommodate this. In general, the O antigen repeating unit structures were chemically simple with di- or trisaccharide backbones. Serological specificity was often provided solely by the presence or absence of an O-acetyl substituent, or a change in the linkage between two sugar residues. Five of the O serotypes in the new scheme were represented by 12 of the 29 reference strains, while three reference strains lacked O antigens altogether, resulting in the elimination of 10 of the original O types. In contrast, the K antigen repeating unit structures were more complex and chemically diverse, having at least four sugar residues. Three K types were each seen in two reference strains while 12 of the 29 reference strains were acapsular. Thus, the resulting schemes contain 19 O types and 14 K types and allow the definitive serotype identification of S. marcescens.
Lipopolysaccharide, antigen, LPS, structure, K-antigen, O-antigen, capsular polysaccharide, Serratia marcescens, Serratia, serotyping, O-serotype
NCBI PubMed ID: 9534235Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: haucken@phls.co.uk
Institutions: Laboratory of Hospital Infection, Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University, Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, chromatography, Quellung reaction, serum adsorption assays
- Article ID: 2955
Oxley D, Wilkinson SG "Structural studies of an acidic galactomannan from the reference strain for Serratia marcescens serogroup O4" -
Carbohydrate Research 179 (1988) 341-348
An acidic, partially acetylated galactomannan has been isolated from the lipopolysaccharide of the reference strain (C.D.C. 864-57) for Serratia marcescens serogroup O4. From the results of methylation analysis, Smith degradations, and n.m.r. spectroscopic studies of the O-deacetylated polymer, it was concluded that the repeating unit has the structure shown, in which the acetal-linked pyruvic acid has the R configuration. The polymer is believed to confer O specificity on the organism, but not to constitute the side chain of the lipopolysaccharide (formula, see text).
Publication DOI: 10.1016/0008-6215(88)84130-2Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, The University, Hull HU6 7RX Great Britain
Methods: NMR
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9. Compound ID: 2274
|
R-Pyr-(2-6:2-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1-3)-a-D-Galp2(%)Ac4(%)Ac-(1-3)-+
|
-4)-a-L-Fucp-(1-4)-a-L-Fucp-(1-3)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_36,SB_7,SB_86
The structure is contained in the following publication(s):
- Article ID: 759
Cescutti P, Toffanin R, Pollesello P, Sutherland IW "Structural determination of the acidic exopolysaccharide produced by a Pseudomonas sp. strain 1.15" -
Carbohydrate Research 315(1-2) (1999) 159-168
Pseudomonas strain 1.15 was isolated from a freshwater biofilm and shown to produce considerable amounts of an acidic polysaccharide which was investigated by methylation analysis, NMR spectroscopy and ionspray mass spectrometry (ISMS). The polysaccharide was depolymerised by a bacteriophage-associated endoglucosidase and by autohydrolysis, and the resulting oligosaccharides were investigated by NMR spectroscopy and mass spectrometry. The resulting data showed that the parent repeating unit of the 1.15 exopolysaccharide (EPS) is a branched hexasaccharide. The main chain is constituted of the trisaccharide -4)-a-L-Fucp-(1-4)-a-L-Fucp-(1-3)-b-D-Glcp-(1- and the side chain a-D-Galp-(1-4)-b-D-GlcAp-(1-3)-a-D-Galp-(1- is linked to O-3 of the first Fuc residue. The terminal non-reducing Gal carries a 1-carboxyethylidene acetal in the R configuration at the positions 4 and 6. Of the four different O-acetyl groups present in non-stoichiometric amounts, two were established to be on O-2 of the 3-linked Gal and on O-2 of the 4-linked Fuc.
structure, strain, structural, Pseudomonas, acidic, determination, structural determination, NMR spectroscopy, exopolysaccharide, acidic exopolysaccharide
NCBI PubMed ID: 10385979Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: cescutti@bbcm.univ.trieste.it
Institutions: Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Universita` di Trieste, Trieste, Italy, Centro Ricerche POLY-bio`s, Area di Ricerca, Trieste, Italy, Cardiovascular Drug Discovery, Department of Pharmacology, Orion Corporation, Espoo, Finland, Institute of Cell and Molecular Biology, Edinburgh University, Edinburgh, UK, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Universita di Trieste, Trieste, Italy, Centro Ricerche POLY-bios, Area di Ricerca, Trieste, Italy
Methods: NMR-2D, methylation, NMR, sugar analysis, ESI-MS, MS, autohydrolysis, enzymatic depolymerization
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10. Compound ID: 2276
|
R-Pyr-(2-6:2-4)-a-D-Galp-(1-4)-b-D-GlcpA-(1-3)-a-D-Galp-(1-3)-a-L-Fucp-(1-4)-a-L-Fucp-(1-3)-D-Glc |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_7,SB_86
The structure is contained in the following publication(s):
- Article ID: 759
Cescutti P, Toffanin R, Pollesello P, Sutherland IW "Structural determination of the acidic exopolysaccharide produced by a Pseudomonas sp. strain 1.15" -
Carbohydrate Research 315(1-2) (1999) 159-168
Pseudomonas strain 1.15 was isolated from a freshwater biofilm and shown to produce considerable amounts of an acidic polysaccharide which was investigated by methylation analysis, NMR spectroscopy and ionspray mass spectrometry (ISMS). The polysaccharide was depolymerised by a bacteriophage-associated endoglucosidase and by autohydrolysis, and the resulting oligosaccharides were investigated by NMR spectroscopy and mass spectrometry. The resulting data showed that the parent repeating unit of the 1.15 exopolysaccharide (EPS) is a branched hexasaccharide. The main chain is constituted of the trisaccharide -4)-a-L-Fucp-(1-4)-a-L-Fucp-(1-3)-b-D-Glcp-(1- and the side chain a-D-Galp-(1-4)-b-D-GlcAp-(1-3)-a-D-Galp-(1- is linked to O-3 of the first Fuc residue. The terminal non-reducing Gal carries a 1-carboxyethylidene acetal in the R configuration at the positions 4 and 6. Of the four different O-acetyl groups present in non-stoichiometric amounts, two were established to be on O-2 of the 3-linked Gal and on O-2 of the 4-linked Fuc.
structure, strain, structural, Pseudomonas, acidic, determination, structural determination, NMR spectroscopy, exopolysaccharide, acidic exopolysaccharide
NCBI PubMed ID: 10385979Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: cescutti@bbcm.univ.trieste.it
Institutions: Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Universita` di Trieste, Trieste, Italy, Centro Ricerche POLY-bio`s, Area di Ricerca, Trieste, Italy, Cardiovascular Drug Discovery, Department of Pharmacology, Orion Corporation, Espoo, Finland, Institute of Cell and Molecular Biology, Edinburgh University, Edinburgh, UK, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Universita di Trieste, Trieste, Italy, Centro Ricerche POLY-bios, Area di Ricerca, Trieste, Italy
Methods: NMR-2D, methylation, NMR, sugar analysis, ESI-MS, MS, autohydrolysis, enzymatic depolymerization
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11. Compound ID: 2277
Structure type: polymer chemical repeating unit
; 180000
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 762
Cérantola S, Marty N, Montrozier H "Structural studies of the acidic exopolysaccharide produced by a mucoid strain of Burkholderia cepacia, isolated from cystic fibrosis" -
Carbohydrate Research 285 (1996) 59-67
The acidic exopolysaccharide produced by a mucoid strain of Burkholderia cepacia isolated from a cystic fibrosis patient, was purified by cetyltrimethylammonium bromide precipitation and/or anion-exchange chromatography. Based on the sugar composition and permethylation analyses, supported by GLC-MS and NMR spectroscopy analyses, the repeating-unit of the polysaccharide was established as →3)-β-D-Glcp-(1→3)-[4,6-O-(1-carboxyethylidene)]-α-D-Galp-(1→.
strain, structural, Burkholderia, Burkholderia cepacia, acidic, exopolysaccharide, pyruvate acetal, structural studies, cystic fibrosis, acidic exopolysaccharide, mucoid, Pseudomonas cepacia
NCBI PubMed ID: 9011377Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Departement des Glycoconjugues et Biomembranes, Laboratoire de Pharmacologie et Toxicologie Fondamentales du CNRS, Toulouse, France
Methods: NMR-2D, GLC-MS, NMR, sugar analysis, anion-exchange chromatography, permethylation
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12. Compound ID: 2796
|
R-Pyr-(2-6:2-4)-+
|
-3)-b-D-Glcp-(1-3)-a-D-Galp-(1-
|
Suc-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: marginalan
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 978
Matulová M, Navarini L, Osman SF, Fett WF "NMR analysis of galactoglucan from Pseudomonas marginalis: assignment of the 1H and 13C NMR spectra and location of succinate groups" -
Carbohydrate Research 283 (1996) 195-205
no abstract
NMR, structure, Marginalan, galactoglucan, Pseudomonas marginalis, succinate
NCBI PubMed ID: 8901271Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovak Republic
Methods: NMR
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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13. Compound ID: 2797
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 978
Matulová M, Navarini L, Osman SF, Fett WF "NMR analysis of galactoglucan from Pseudomonas marginalis: assignment of the 1H and 13C NMR spectra and location of succinate groups" -
Carbohydrate Research 283 (1996) 195-205
no abstract
NMR, structure, Marginalan, galactoglucan, Pseudomonas marginalis, succinate
NCBI PubMed ID: 8901271Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovak Republic
Methods: NMR
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- 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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14. Compound ID: 2919
|
R-Pyr-(2-6:2-4)-a-D-Galp2(66%)Ac3(64%)Ac-(1-4)-b-D-GlcpA-(1-4)-+
|
-3)-a-D-Galp-(1-6)-b-D-Galp-(1-3)-b-D-Galp-(1-
|
10%b-D-Glcp-(1-6)-+ |
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Structure type: polymer chemical repeating unit
Trivial name: amylovoran
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_423153,IEDB_742248,IEDB_983931,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_36,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1053
Nimtz M, Mort A, Domke T, Wray V, Zhang Y, Qiu F, Coplin D, Geider K "Structure of amylovoran, the capsular exopolysaccharide from the fire blight pathogen Erwinia amylovora" -
Carbohydrate Research 287(1) (1996) 59-76
The acidic exopolysaccharide (EPS) of Erwinia amylovora, amylovoran, was purified from culture supernatants of bacteria in minimal medium and cleaved chemically either by treatment with trifluoracetic acid or hydrofluoric acid, and enzymatically by digestion with depolymerase from E. amylovora phage phi-Ealh. Structural characterization of the resulting oligosaccharides was performed by a combination of mass spectrometric and NMR [one- and two-dimensional (1D and 2D)] spectroscopic techniques. A branched repeating unit with five monosaccharide residues and various substituents was determined: [sequence: see text] The terminal monosaccharide of the side branch, which bears a 4,6-bound pyruvate residue in the R-configuration, was found to be modified with 2-linked (26%), 3-linked (24%), 2-,3-linked (40%) O-acetyl groups, or these were absent (10%). An additional glucose residue is linked to approximately 10% of the core α-galactose of the repeating unit.
Erwinia amylovora, structure, exopolysaccharide, fire blight
NCBI PubMed ID: 8765060Publication DOI: 10.1016/0008-6215(96)00070-5Journal NLM ID: 0043535Publisher: Elsevier
Institutions: GBF, Gesellschaft fur Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany, Oklahoma State University, 246 Noble Research Center, Stillwater, OK 74074, USA, Max-Planck-Institut fur medizinische Forschung, Jahnstrasse 29, D-69120 Heidelberg, Germany, Department of Plant Pathology, Ohio State University, Columbus, OH 43210, USA
Methods: partial acid hydrolysis, NMR, HF solvolysis, ESI-MS/MS, enzymatic depolymerization
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15. Compound ID: 2969
|
R-Pyr-(2-6:2-4)-a-D-Galp2(%)Ac3(%)Ac-(1-4)-b-D-GlcpA-(1-4)-a-D-Galp-(1-6)-b-D-Galp-(1-3)-D-Galp |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_190606,IEDB_423153,IEDB_742248,SB_163,SB_165,SB_166,SB_187,SB_195,SB_36,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1053
Nimtz M, Mort A, Domke T, Wray V, Zhang Y, Qiu F, Coplin D, Geider K "Structure of amylovoran, the capsular exopolysaccharide from the fire blight pathogen Erwinia amylovora" -
Carbohydrate Research 287(1) (1996) 59-76
The acidic exopolysaccharide (EPS) of Erwinia amylovora, amylovoran, was purified from culture supernatants of bacteria in minimal medium and cleaved chemically either by treatment with trifluoracetic acid or hydrofluoric acid, and enzymatically by digestion with depolymerase from E. amylovora phage phi-Ealh. Structural characterization of the resulting oligosaccharides was performed by a combination of mass spectrometric and NMR [one- and two-dimensional (1D and 2D)] spectroscopic techniques. A branched repeating unit with five monosaccharide residues and various substituents was determined: [sequence: see text] The terminal monosaccharide of the side branch, which bears a 4,6-bound pyruvate residue in the R-configuration, was found to be modified with 2-linked (26%), 3-linked (24%), 2-,3-linked (40%) O-acetyl groups, or these were absent (10%). An additional glucose residue is linked to approximately 10% of the core α-galactose of the repeating unit.
Erwinia amylovora, structure, exopolysaccharide, fire blight
NCBI PubMed ID: 8765060Publication DOI: 10.1016/0008-6215(96)00070-5Journal NLM ID: 0043535Publisher: Elsevier
Institutions: GBF, Gesellschaft fur Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany, Oklahoma State University, 246 Noble Research Center, Stillwater, OK 74074, USA, Max-Planck-Institut fur medizinische Forschung, Jahnstrasse 29, D-69120 Heidelberg, Germany, Department of Plant Pathology, Ohio State University, Columbus, OH 43210, USA
Methods: partial acid hydrolysis, NMR, HF solvolysis, ESI-MS/MS, enzymatic depolymerization
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