Found 77 structures.
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1. Compound ID: 946
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Suc-(1-6)-+
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Pyr-(2-6:2-4)-b-Glcp-(1-3)-b-Glcp-(1-3)-b-Glcp-(1-6)-b-Glcp-(1-6)-+
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-4)-b-Glcp-(1-4)-b-Glcp6Ac-(1-4)-b-Glcp-(1-3)-b-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 287
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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2. Compound ID: 1608
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Suc-(1-4)-a-D-Quip4N-(1-4)-+
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-3)-b-D-GlcpNAc-(1-2)-a-D-GalpA-(1-3)-a-L-Rhap-(1-4)-a-D-Glcp-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 498
Kondakova AN, Linder B, Fudala R, Senchenkova SN, Moll H, Shashkov AS, Kaca W, Zähringer U, Knirel YA "New stuctures of the O-specific polysaccharides of Proteus. Part 4. Polysaccharides containing unusual acidic N-acyl derivatives of 4-amino-4,6-dideoxy-D-glucose" -
Biochemistry (Moscow) 69(9) (2004) 1034-1043
The structures of the O-polysaccharides of the lipopolysaccharides of Proteus mirabilis O7 and O49 were determined by chemical methods, mass spectrometry, including MS/MS, and NMR spectroscopy, including experiments run in an H2O/D2O mixture to reveal correlations for NH protons. The O-polysaccharides were found to contain N-carboxyacetyl (malonyl) and N-(3-carboxypropanoyl) (succinyl) derivatives of 4-amino-4,6-dideoxyglucose (4-amino-4-deoxyquinovose, Qui4N), respectively. The behavior of Qui4N derivatives with the dicarboxylic acids under conditions of acid hydrolysis and methanolysis was studied using GLC-MS.
O-polysaccharide, Proteus mirabilis, 6-dideoxy-d-glucose, 4-amino-4, malonic acid, succinic acid, aspartic acid, MS/MS
NCBI PubMed ID: 15521818Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland, Swietokrzyska Academy, Kielce, Poland
Methods: methylation, NMR-2D, NMR, ESI-MS, IRMPD-MS/MS
- Article ID: 4043
Kaca W, Glenska J, Lechowicz L, Grabowski S, Brauner A, Kwinkowski M "Serotyping of Proteus mirabilis clinical strains based on lipopolysaccharide O-polysaccharide and core oligosaccharide structures" -
Biochemistry (Moscow) 76(7) (2011) 851-861
The aim of this work was to serotype Proteus mirabilis urinary tract infection (UTI) strains based on chemically defined O-antigens with the use of two clinical collections from Sweden and Poland consisting of 99 and 24 UTI strains, respectively. A simple two-step serotyping scheme was proposed using enzyme immunoassay with heat-stable surface antigens of Proteus cells and immunoblotting with isolated lipopolysaccharides (LPSs). Using polyclonal anti-P. mirabilis rabbit antisera, 50 Swedish and 8 Polish strains were classified into serogroups O10, O38, O36, O30, O17, O23, O9, O40, O49, O27, O5, O13, O24, O14, and O33. From the Swedish strains, 10 belonged to serogroup O10 and five to each of serogroups O38, O36, and O9. Therefore, none of the O-serogroups was predominant. The majority of the serotyped clinical strains possess acidic O-antigens containing uronic acids and various acidic non-carbohydrate substituents. In immunoblotting, antisera cross-reacted with both O-antigen and core of LPSs. The core region of 19 LPSs bound a single serum, and that of 12 LPSs bound more than two sera. Following bioinformatic analysis of the available sequences, a molecular approach to the prediction of Proteus core oligosaccharide structures was proposed. The identification of the core type of P. mirabilis R110, derived from a serogroup O3 wild strain, using restriction fragments length polymorphism analysis of galacturonic acid transferase is shown as an example. In summary, the most frequent O-serogroups among P. mirabilis UTI stains were identified. The diversity of serological reactions of LPSs is useful for serotyping of P. mirabilis clinical isolates. A possible role of the acidic components of O-antigens in UTI is discussed.
Lipopolysaccharide, O-antigen, Proteus mirabilis, serology, serotyping, glycosyl transferas
NCBI PubMed ID: 21999547Publication DOI: 10.1134/S0006297911070169Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: wieslaw.kaca@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: PCR, SDS-PAGE, EIA, serological methods, immunoblotting, bioinformatic analysis
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3. Compound ID: 2196
Structure type: polymer chemical repeating unit
; >300000
Compound class: EPS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_753248
The structure is contained in the following publication(s):
- Article ID: 708
Joyce JG, Abeygunawardana C, Xu Q, Cook JC, Hepler R, Przysiecki CT, Grimm KM, Roper K, Ip CC, Cope L, Montgomery D, Chang M, Campie S, Brown M, McNeely TB, Zorman J, Maira-Litran T, Pier GB, Keller PM, Jansen KU, Mark GE "Isolation, structural characterization, and immunological evaluation of a high-molecular-weight exopolysaccharide from Staphylococcus aureus" -
Carbohydrate Research 338(9) (2003) 903-922
Colonization of implanted medical devices by coagulase-negative staphylococci such as Staphylococcus epidermidis is mediated by the bacterial polysaccharide intercellular adhesin (PIA), a polymer of β-(1→6)-linked glucosamine substituted with N-acetyl and O-succinyl constituents. The icaADBC locus containing the biosynthetic genes for production of PIA has been identified in both S. epidermidis and S. aureus. Whereas it is clear that PIA is a constituent that contributes to the virulence of S. epidermidis, it is less clear what role PIA plays in infection with S. aureus. Recently, identification of a novel polysaccharide antigen from S. aureus termed poly N-succinyl β-(1→6)-glucosamine (PNSG) has been reported. This polymer was composed of the same glycan backbone as PIA but was reported to contain a high proportion of N-succinylation rather than acetylation. We have isolated a glucosamine-containing exopolysaccharide from the constitutive over- producing MN8m strain of S. aureus in order to prepare polysaccharide- protein conjugate vaccines. In this report we demonstrate that MN8m produced a high-molecular-weight (>300,000 Da) polymer of β-(1→6)- linked glucosamine containing 45-60% N-acetyl, and a small amount of O- succinyl (approx 10% mole ratio to monosaccharide units). By detailed NMR analyses of polysaccharide preparations, we show that the previous identification of N-succinyl was an analytical artifact. The exopolysaccharide we have isolated is active in in vitro hemagglutination assays and is immunogenic in mice when coupled to a protein carrier. We therefore conclude that S. aureus strain MN8m produces a polymer that is chemically and biologically closely related to the PIA produced by S. epidermidis
Staphylococcus, Staphylococcus aureus, High-molecular-weight exopolysaccharide, Polysaccharide intercellular adhesin
NCBI PubMed ID: 12681914Publication DOI: 10.1016/s0008-6215(03)00045-4Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: joseph_joyce@merck.com
Institutions: Departments of Virus and Cell Biology, Bioprocess and Bioanalytical Research, Merck Research Laboratories, WP16-107, P.O. Box 4, 19486, West Point, PA, USA
Methods: NMR
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4. Compound ID: 2289
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Suc-(1-6)-+
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Pyr-(2-6:2-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-4)-b-D-Glcp6Ac-(1-4)-b-D-Glcp-(1-3)-D-Galp |
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Structure type: oligomer
Trivial name: succinoglucan
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 770
Chouly C, Colquhoun IJ, Jodelet A, York G, Walker GC "NMR studies of succinoglycan repeating-unit octasaccharides from Rhizobium meliloti and Agrobacterium radiobacter" -
International Journal of Biological Macromolecules 17 (1995) 357-363
Complete 1H and 13C-nuclear magnetic resonance assignments have been obtained for the octasaccharide repeating units of the bacterial polysaccharide succinoglycan from Rhizobium meliloti Rm1021 and Agrobacterium radiobacter NCIB 11883. The assignments were used to determine the locations of the O-succinyl and O-acetyl substituents. The O-acetyl substituent in Rm1021 was attached to the 3rd residue from the reducing end, and the O-succinyl group was attached to the 7th residue in both octasaccharides. The structure of the Rm1021 octasaccharide is as shown below: [formula: see text] A small amount of succinate was also attached to C6 of the 6th residue in both octasaccharides.
NMR, structure, polysaccharide, repeating unit, Rhizobia, Rhizobium, extracellular, Rhizobium meliloti, Agrobacterium, Agrobacterium radiobacter, succinoglycan
NCBI PubMed ID: 8789340Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Institutions: Institute of Food Research, Norwich Laboratory, UK
Methods: NMR-2D, NMR
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5. Compound ID: 2290
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Suc-(1-6)-+
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Pyr-(2-6:2-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
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-4)-b-D-Glcp-(1-4)-b-D-Glcp6Ac-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: succinoglycan
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 770
Chouly C, Colquhoun IJ, Jodelet A, York G, Walker GC "NMR studies of succinoglycan repeating-unit octasaccharides from Rhizobium meliloti and Agrobacterium radiobacter" -
International Journal of Biological Macromolecules 17 (1995) 357-363
Complete 1H and 13C-nuclear magnetic resonance assignments have been obtained for the octasaccharide repeating units of the bacterial polysaccharide succinoglycan from Rhizobium meliloti Rm1021 and Agrobacterium radiobacter NCIB 11883. The assignments were used to determine the locations of the O-succinyl and O-acetyl substituents. The O-acetyl substituent in Rm1021 was attached to the 3rd residue from the reducing end, and the O-succinyl group was attached to the 7th residue in both octasaccharides. The structure of the Rm1021 octasaccharide is as shown below: [formula: see text] A small amount of succinate was also attached to C6 of the 6th residue in both octasaccharides.
NMR, structure, polysaccharide, repeating unit, Rhizobia, Rhizobium, extracellular, Rhizobium meliloti, Agrobacterium, Agrobacterium radiobacter, succinoglycan
NCBI PubMed ID: 8789340Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Institutions: Institute of Food Research, Norwich Laboratory, UK
Methods: NMR-2D, NMR
- Article ID: 1291
Yamazaki M, Thorne L, Mikolajczak M, Armentrout RW, Pollock TJ "Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88" -
Journal of Bacteriology 178 (1996) 2676-2687
Several structurally related capsular polysaccharides that are secreted by members of the genus Sphingomonas are being developed as aqueous rheological control agents for diverse industrial and food applications. They include gellan (S-60), welan (S-130), rhamsan (S-194), S-657, S-88, S-198, S-7, and NW-11. We refer to these polysaccharides as sphingans, after the genus name. This paper characterizes the first gene cluster isolated from a Sphingomonas species (S88) that is required for capsule synthesis. Overlapping DNA segments which spanned about 50 kbp of S88 DNA restored the synthesis of sphingan S-88 in capsule-negative mutants. The mutations were mapped into functional complementation groups, and the contiguous nucleotide sequence for the 29-kbp cluster was determined. The genetic complementation map and the DNA sequences were interpreted as an extended multicistronic locus containing genes essential for the assembly and secretion of polysaccharide S-88. Many of the deduced amino acid sequences were similar to gene products from other polysaccharide-secreting bacteria such as Rhizobium meliloti (succinoglycan), Xanthomonas campestris (xanthan gum), and Salmonella enterica (O antigen). The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans. Unexpectedly, there were also two genes for secretion of a lytic or toxin-like protein nested within the polysaccharide cluster. The conservation and linkage of genes that code for a defensive capsule and genes for secretion of an offensive lysin or toxin suggest a heretofore unknown pathogenic life history for Sphingomonas strain S88
biosynthesis, synthesis, gene, strain, polysaccharide, Sphingomonas, linkage, capsule
NCBI PubMed ID: 8626338Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Shin-Etsu Bio, Inc., San Diego, California 92121, USA
- Article ID: 3110
Reuber TL, Walker GC "Biosynthesis of succinoglycan, a symbiotically important exopolysaccharide of Rhizobium meliloti" -
Cell 74 (1993) 269-280
The exo genes of Rhizobium meliloti are needed for the synthesis of an acidic exopolysaccharide, succinoglycan. We have assigned biosynthetic roles to the products of the exo genes by characterizing succinoglycan biosynthetic intermediates from exo mutant strains. We propose a model of succinoglycan biosynthesis in which the products of the exoY and exoF genes function in the addition of the first sugar, galactose, to the lipid carrier; the products of the exoA, exoL, exoM, exoO, exoU, and exoW genes function in subsequent sugar additions; and the product of the exoV gene functions in the addition of pyruvate. The products of the exoP, exoQ, and exoT genes are required for polymerization of the octasaccharide subunits or transport of the completed polymer.
NCBI PubMed ID: 8343955Publication DOI: 10.1016/0092-8674(93)90418-pJournal NLM ID: 0413066Publisher: Cambridge, MA: Cell Press
Institutions: Department of Biology, Massachusetts Institute of Technology, Cambridge, MA, USA
- Article ID: 3126
Reuber TL, Walker GC "The acetyl substituent of succinoglycan is not necessary for alfalfa nodule invasion by Rhizobium meliloti Rm1021" -
Journal of Bacteriology 175 (1993) 3653-3655
Rhizobium meliloti Rm1021 requires a Calcofluor-binding exopolysaccharide, termed succinoglycan or EPS I, to invade alfalfa nodules. We have determined that a strain carrying a mutation in the exoZ locus produces succinoglycan that lacks the acetyl substituent. The exoZ mutant nodules alfalfa normally.
NCBI PubMed ID: 8501069Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Department of Biology, Massachusetts Institute of Technology, Cambridge, MA, USA
- Article ID: 3127
Reinhold BB, Chan SY, Reuber TL, Marra A, Walker GC, Reinhold VN "Detailed structural characterization of succinoglycan, the major exopolysaccharide of Rhizobium meliloti Rm1021" -
Journal of Bacteriology 176 (1994) 1997-2002
The detailed structure of the symbiotically important exopolysaccharide succinoglycan from Rhizobium meliloti Rm1021 was determined by mass spectrometry with electrospray ionization and collision-induced dissociation of the octameric oligosaccharide repeating unit. Previously undetermined locations of the succinyl and acetyl modifications were determined, in respect to both residue locations within the octamer and the carbon positions within the pyranose ring. Glycosidic linkages determined previously by methylation analysis were also verified.
NCBI PubMed ID: 8144468Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Department of Nutrition, Harvard School of Public Health, Boston, Massachusetts 02115
Methods: methylation, ESI-MS, ESI-CID-MS
- Article ID: 3280
Leigh JA, Walker GC "Exopolysaccharides of Rhizobium: Synthesis, regulation and symbiotic function" -
Trends in Genetics 10(2) (1994) 63-67
Exopolysaccharides of Rhizobium have long been suspected, and are now known, to function in the Rhizobium-legume root nodule symbiosis. Recent studies have enhanced our knowledge of these extracellular polymers as symbiotic signals and have elucidated their biosynthesis and regulation.
biosynthesis, synthesis, polysaccharide, polymer, enhanced, regulation, Rhizobia, Rhizobium, exopolysaccharide, exopolysaccharides, function, review, extracellular, Polymers, symbiotic
NCBI PubMed ID: 8191588Journal NLM ID: 8507085Publisher: Elsevier
Institutions: Department of Microbiology, University of Washington, Seattle 98195.
Methods: genetic methods, biochemical methods
- Article ID: 5400
Becker A, Puhler A "Production of exopolysaccharides" -
Book: The Rhizobiaceae. Molecular Biology of Model Plant-Associated Bacteria (1998) Chapter 6, 97-118
A broad variety of bacteria including the Rhizobiaceae are able to secrete polysaccharides. Sugar polymers that form an adherent cohesive layer on the cell surface are designated capsular polysacharides (CPS), whereas the term exopolysaccharide (EPS) is used for polysaccharides with little or no cell association. Due to the variation of monosaccharide sequences, condensation linkages and non-carbohydrate decorations, an infinite array of structures can be provided by this class of macromolecules. Different rheological properties depend on the structure and the molecular weight of EPS. These properties and the location of EPS, forming the outer layer of the cell surface, contribute to the cell protection against environmental influences, attachment to surfaces, nutrient gathering and to antigenicity (Costerton et al., 1987, Sutherland 1988, Whitfield 1988, Beveridge and Graham 1991). The structural diversity of oligosaccharides derived from EPS enables them to function additionally as informational molecules in cell-cell-communications. Finally, many symbiotic bacteria of the Rhizobiaceae use oligosaccharides as signal molecules in the interaction with their host plant.
glycosyl transferase, Indeterminate Nodule, Symbiotic Phenotype, Exopolysaccharide Biosynthesis, SU47 Mutant
WWW link: https://link.springer.com/chapter/10.1007/978-94-011-5060-6_6Publisher: Dordrecht: Kluwer Academic Publishers
Correspondence: hippo@genetik.uni-bielefeld.de
Editors: Spaink HP, Kondorosi A, Hooykaas PJJ
Institutions: Lehrstuhl für Genetik, Fakultät für Biologie, Universität Bielefeld, Germany
- Article ID: 5492
Schmid J, Sieber V, Rehm B "Bacterial exopolysaccharides: biosynthesis pathways and engineering strategies" -
Frontiers in Microbiology 6 (2015) 496
Bacteria produce a wide range of exopolysaccharides which are synthesized via different biosynthesis pathways. The genes responsible for synthesis are often clustered within the genome of the respective production organism. A better understanding of the fundamental processes involved in exopolysaccharide biosynthesis and the regulation of these processes is critical toward genetic, metabolic and protein-engineering approaches to produce tailor-made polymers. These designer polymers will exhibit superior material properties targeting medical and industrial applications. Exploiting the natural design space for production of a variety of biopolymer will open up a range of new applications. Here, we summarize the key aspects of microbial exopolysaccharide biosynthesis and highlight the latest engineering approaches toward the production of tailor-made variants with the potential to be used as valuable renewable and high-performance products for medical and industrial applications.
biosynthesis, gene clusters, Bacterial exopolysaccharides, polysaccharide engineering, tailor-made exopolysaccharides
NCBI PubMed ID: 26074894Publication DOI: 10.3389/fmicb.2015.00496Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Jochen Schmid
Institutions: Chair of Chemistry of Biogenic Resources, Technische Universität München Straubing, Germany, Institute of Fundamental Sciences, Massey University Palmerston North, New Zealand, The MacDiarmid Institute for Advanced Materials and Nanotechnology Palmerston North, New Zealand
- Article ID: 6248
Jeong JP, Kim Y, Hu Y, Jung S "Bacterial Succinoglycans: Structure, Physical Properties, and Applications" -
Polymers 14(2) (2022) 276
Succinoglycan is a type of bacterial anionic exopolysaccharide produced from Rhizobium, Agrobacterium, and other soil bacteria. The exact structure of succinoglycan depends in part on the type of bacterial strain, and the final production yield also depends on the medium composition, culture conditions, and genotype of each strain. Various bacterial polysaccharides, such as cellulose, xanthan, gellan, and pullulan, that can be mass-produced for biotechnology are being actively studied. However, in the case of succinoglycan, a bacterial polysaccharide, relatively few reports on production strains or chemical and structural characteristics have been published. Physical properties of succinoglycan, a non-Newtonian and shear thinning fluid, have been reported according to the ratio of substituents (pyruvyl, succinyl, acetyl group), molecular weight (Mw), and measurement conditions (concentration, temperature, pH, metal ion, etc.). Due to its unique rheological properties, succinoglycan has been mainly used as a thickener and emulsifier in the cosmetic and food industries. However, in recent reports, succinoglycan and its derivatives have been used as functional biomaterials, e.g., in stimuli-responsive drug delivery systems, therapeutics, and cell culture scaffolds. This suggests a new and expanded application of succinoglycan as promising biomaterials in biomedical fields, such as tissue engineering, regenerative medicine, and pharmaceuticals using drug delivery.
bacterial polysaccharides, succinoglycan, application, Biomaterials, hydrogels
NCBI PubMed ID: 35054683Publication DOI: 10.3390/polym14020276Journal NLM ID: 101545357Publisher: Basel: MDPI
Correspondence: Seunho Jung
Institutions: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, Seoul 05029, Korea, Department of Systems Biotechnology, Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea
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6. Compound ID: 2798
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R-Pyr-(2-6:2-4)-+
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-3)-b-D-Glcp-(1-3)-a-D-Galp-(1-
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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_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 979
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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7. Compound ID: 2800
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 979
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
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8. Compound ID: 3588
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Pyr-(2-6:2-4)-+
|
-3)-b-D-Glcp-(1-3)-a-D-Galp-(1-
|
Suc-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Trivial name: marginalan
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 1346
Abatangelo A, Gilli R, Navarini L, Rizzo R, Osman SF, Fett WF "Solution properties of the exopolysaccharide produced by Pseudomonas marginalis strain HT041B" -
Journal of Carbohydrate Chemistry 16(4-5) (1997) 583-598
The solution properties of the exopolysaccharide marginalan produced by Pseudomonas marginalis HT041B were investigated by means of low-angle laser light-scattering, capillary viscometry, and rheology. Potentiometric and viscosimetric data indicated the absence of a cooperative transition of the disorder-to-order type. The experimental findings obtained in dilute solution (Mark-Houwink coefficients, rigidity coefficient, characteristic ratio) suggested that the polymer behaves like a semiflexible chain which adopts a disordered conformation. The rheological behaviour of more concentrated marginalan solutions, as determined by means of both steady shear and oscillatory measurements, further confirmed the disordered conformational state of the polymer in solution.
strain, Pseudomonas, property, exopolysaccharide, solution, solution properties, Pseudomonas marginalis
Publication DOI: 10.1080/07328309708007337Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Dipartimento BBCM, University of Trieste, Trieste, Italy
Methods: light scattering, rheological measurements, capillary viscosimetry
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9. Compound ID: 4241
|
Suc-(1-4)-a-D-Quip4N-(1-4)-+
|
-2)-a-D-GalpA-(1-3)-a-L-Rhap-(1-4)-a-D-Glcp-(1-2)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-
Suc = 3-carboxypropionyl (succinyl) |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1587
Zablotni A, Perepelov AV, Knirel YA, Sidorczyk Z "Structure of the O-polysaccharide of Proteus mirabilis OC (CCUG 10702) from a new proposed Proteus serogroup O75" -
Carbohydrate Research 340(11) (2005) 1908-1913
A neutral O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Proteus mirabilis OC (CCUG 10702) and studied by sugar and methylation analyses and (1)H and (13)C NMR spectroscopy. The following structure of the tetrasaccharide repeating unit of the polysaccharide was established: [structure: see text]. Based on the unique structure of the O-polysaccharide and serological data, we propose classifying P. mirabilis OC (CCUG 10702) into a new separate Proteus serogroup O75. A weak cross-reaction of O-antiserum against P. mirabilis OC with the lipopolysaccharide of P. mirabilis O49 was accounted for by a similarity in the O-polysaccharide structures.
Lipopolysaccharide, structure, epitope, O-polysaccharide, O-specific polysaccharide, Proteus mirabilis, O-serogroup
NCBI PubMed ID: 15979596Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland
Methods: methylation, NMR, sugar analysis
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10. Compound ID: 6454
|
Suc-(1-6)-+
|
S-Pyr-(2-6:2-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: succinoglycan
Compound class: EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1674
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
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11. Compound ID: 6455
|
Suc-(1-6)-+
|
S-Pyr-(2-6:2-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: succinoglycan
Compound class: EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1674
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
- 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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12. Compound ID: 6552
|
Suc-(1-6)-+
|
S-Pyr-(2-6:2-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-b-D-Glcp-(1-6)-b-D-Glcp-(1-6)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Glcp6Ac-(1-4)-b-D-Glcp-(1-3)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: succinoglycan
Compound class: EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2963
Matulová M, Toffanin R, Navarini L, Gilli R, Paoletti S, Cesaro A "NMR analysis of succinoglycans from different microbial sources: partial assignment of their 1H and 13C NMR spectra and location of the succinate and the acetate groups" -
Carbohydrate Research 265 (1994) 167-179
In order to obtain information on the location of succinate and acetate groups, comparative NMR analyses were carried out on succinoglycans from different microbial sources by using conventional and advanced NMR techniques. In particular, one-dimensional, 1H and 13C NMR spectra were recorded for qualitative and quantitative analysis on native high-molecular-weight succinoglycans (both in the Na+ salt and free-acid forms) from Pseudomonas sp. NCIB 11592, Agrobacterium radiobacter A201-25, Rhizobium meliloti YE-2, and Rhizobium sp. isolated from Vicia faba and compared with those of the deacylated and deacylated-depyruvated, partially depolymerised exopolysaccharides from Rhizobium meliloti YE-2. Moreover, a series of two-dimensional experiments was performed on all the exopolysaccharides aiming at the partial assignment of the NMR spectra. The NMR data showed that succinate is located on O-6 of either one or both of the two side chain 3-linked β-D-Glc residues, whereas the acetate (when it is present) is located on one of the O-6 of backbone 4-linked β-D-Glc units, but the specific site could not be determined. In addition, the spectral features of the succinate substituent were found to be sensitive to pH changes.
NMR analysis, Succinoglycans, an NMR analysis of
NCBI PubMed ID: 7842440Publication DOI: 10.1016/0008-6215(94)00227-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Centro Ricerche POLY-biós LBT-Area di Ricerca, Padriciano 99, I-34012 Trieste, Italy, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, deacylation
- Article ID: 6412
Kelly SD, Ovchinnikova OG, Muller F, Steffen M, Braun M, Sweeney RP, Kowarik M, Follador R, Lowary TL, Serventi F, Whitfield C "Identification of a second glycoform of the clinically prevalent O1 antigen from Klebsiella pneumoniae" -
Proceedings of the National Academy of Sciences of the USA 120(29) (2023) e2301302120
Carbapenemase and extended beta-lactamase-producing Klebsiella pneumoniae isolates represent a major health threat, stimulating increasing interest in immunotherapeutic approaches for combating Klebsiella infections. Lipopolysaccharide O antigen polysaccharides offer viable targets for immunotherapeutic development, and several studies have described protection with O-specific antibodies in animal models of infection. O1 antigen is produced by almost half of clinical Klebsiella isolates. The O1 polysaccharide backbone structure is known, but monoclonal antibodies raised against the O1 antigen showed varying reactivity against different isolates that could not be explained by the known structure. Reinvestigation of the structure by NMR spectroscopy revealed the presence of the reported polysaccharide backbone (glycoform O1a), as well as a previously unknown O1b glycoform composed of the O1a backbone modified with a terminal pyruvate group. The activity of the responsible pyruvyltransferase (WbbZ) was confirmed by western immunoblotting and in vitro chemoenzymatic synthesis of the O1b terminus. Bioinformatic data indicate that almost all O1 isolates possess genes required to produce both glycoforms. We describe the presence of O1ab-biosynthesis genes in other bacterial species and report a functional O1 locus on a bacteriophage genome. Homologs of wbbZ are widespread in genetic loci for the assembly of unrelated glycostructures in bacteria and yeast. In K. pneumoniae, simultaneous production of both O1 glycoforms is enabled by the lack of specificity of the ABC transporter that exports the nascent glycan, and the data reported here provide mechanistic understanding of the capacity for evolution of antigenic diversity within an important class of biomolecules produced by many bacteria.
Lipopolysaccharide, O antigen, Klebsiella pneumoniae, antigenic diversity, vaccine candidate
NCBI PubMed ID: 37428935Publication DOI: 10.1073/pnas.2301302120Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: F. Serventi
; C. Whitfield
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON N1G 2W1, Canada, LimmaTech Biologics AG, Schlieren 8952, Switzerland, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada, Institute of Biological Chemistry, Academia Sinica, Taipei, Nangang 11529, Taiwan, Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, ESI-MS, mild acid hydrolysis, Western blotting, genetic methods, enzyme assay, LC-MS, bioinformatic analysis, SEC, phylogenetic analysis, monoclonal antibodies
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13. Compound ID: 6767
|
Pyr-(2-6:2-4)-+
|
Suc-(1-?)-+ |
| |
-3)-b-D-Glcp-(1-3)-a-D-Galp-(1- |
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_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 233
Fett WF, Wells JM, Cescutti P, Wijey C "Identification of exopolysaccharides produced by fluorescent pseudomonads associated with commercial mushroom (Agaricus bisporus) production" -
Applied and Environmental Microbiology 61 (1995) 513-517
The acidic exopolysaccharides (EPSs) from 63 strains of mushroom production-associated fluorescent pseudomonads which were mucoid on Pseudomonas agar F medium (PAF) were isolated, partially purified, and characterized. The strains were originally isolated from discolored lesion which developed postharvest on mushroom (Agaricus bisporus) caps or from commercial lots of mushroom casing medium. An acidic galactoglucan, previously named marginalan, was produced by mucoid strains of the saprophyte Pseudomonas putida and the majority of mucoid strains of saprophytic P. fluorescens (biovars III and V) isolated from casing medium. One biovar II strain (J1) of P. fluorescens produced alginate, a copolymer of mannuronic and guluronic acids, and one strain (H13) produced an apparently unique EPS containing neutral and amino sugars. Of 10 strains of the pathogen "P. gingeri," the causal agent of mushroom ginger blotch, 8 gave mucoid growth on PAF. The "P. gingeri" EPS also was unique in containing both neutral sugar and glucuronic acid. Mucoid, weakly virulent strains of "P. reactans" produced either alginate or marginalan. All 10 strains of the pathogen P. tolaasii, the causal agent of brown blotch of mushrooms were nonnmucoid on PAF. Production of EPS by these 10 strains plus the 2 nonmucoid strains of "P. gingeri" also was negative on several additional solid media as well as in two broth media tested. The results support our previous studies indicating that fluorescent pseudomonads are a rich source of novel EPSs.
Pseudomonas, exopolysaccharide, exopolysaccharides, identification, production, fluorescent, mushroom
NCBI PubMed ID: 7574589Journal NLM ID: 7605801Publisher: American Society for Microbiology
Institutions: Eastern Regional Research Center, U.S. Department of Agriculture, Philadelphia, Pennsulvania 19118, USA, Departement of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Trieste, Italy
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14. Compound ID: 7369
|
b-D-Glcp-(1-3)-+
|
/Variants 0/-+ |
| |
/Variants 1/-+ | |
| | |
/Variants 4/-+ /Variants 2/-+ | | b-D-Glcp-(1-3)-+ Suc-(1-3)-+ | Suc-(1-3)-+ Oco-(1-1)-+
| | | | | | | | |
/Variants 3/-a-D-Glcp3Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp6Me-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-D-GroA
/Variants 0/ is:
iBut-(1-6)-
OR (exclusively)
Pp-6)-
OR (exclusively)
Ac-6)-
/Variants 1/ is:
iBut-(1-6)-
OR (exclusively)
Pp-6)-
OR (exclusively)
Ac-6)-
/Variants 2/ is:
iBut-(1-6)-
OR (exclusively)
Pp-6)-
OR (exclusively)
Ac-6)-
/Variants 3/ is:
iBut-(1-6)-
OR (exclusively)
Pp-6)-
OR (exclusively)
Ac-6)-
/Variants 4/ is:
iBut-(1-4)-
OR (exclusively)
Pp-4)-
OR (exclusively)
Ac-4)- |
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Structure type: oligomer
Trivial name: polymethylated polysaccharide
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3338
Stadthagen G, Sambou T, Guerin M, Barilone N, Boudou F, Kordulakova J, Charles P, Alzari PM, Lemassu A, Daffé M, Puzo G, Gicquel B, Rivière M, Jackson M "Genetic basis for the biosynthesis of methylglucose lipopolysaccharides in Mycobacterium tuberculosis" -
Journal of Biological Chemistry 282(37) (2007) 27270-27276
Mycobacteria produce two unusual polymethylated polysaccharides, the 6-O-methylglucosyl-containing lipopolysaccharides (MGLP) and the 3-O-methylmannose polysaccharides, which have been shown to regulate fatty acid biosynthesis in vitro. A cluster of genes dedicated to the synthesis of MGLP was identified in Mycobacterium tuberculosis and Mycobacterium smegmatis. Overexpression of the putative glycosyltransferase gene Rv3032 in M. smegmatis greatly stimulated MGLP production, whereas the targeted disruption of Rv3032 in M. tuberculosis and that of the putative methyltransferase gene MSMEG2349 in M. smegmatis resulted in a dramatic reduction in the amounts of MGLP synthesized and in the accumulation of precursors of these molecules. Disruption of Rv3032 also led to a significant decrease in the glycogen content of the tubercle bacillus, indicating that the product of this gene is likely to be involved in the elongation of more than one α-(1→4)-glucan in this bacterium. Results thus suggest that Rv3032encodes the α-(1→4)-glucosyltransferase responsible for the elongation of MGLP, whereas MSMEG2349 encodes the O-methyltransferase required for the 6-O-methylation of these compounds
gene, Mycobacterium smegmatis, 3-O-methylmannose
NCBI PubMed ID: 17640872Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Mary.Jacson@colostate.edu
Institutions: UnitedeGenetique Mycobacterienne and Unite de Biochimie Structurale, Institut Pasteur, 75015 Paris, France
Methods: MALDI-TOF MS, genetic methods
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15. Compound ID: 7472
Structure type: polymer chemical repeating unit
Compound class: phosphoglycan
Contained glycoepitopes: IEDB_135394,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_150077,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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