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Structure type: polymer chemical repeating unit
Compound class: CPS

• Article ID: 3407
  Gilbert M, Mandrell RE, Parker CT, Li J, Vinogradov E "Structural analysis of the capsular polysaccharide from Campylobacter jejuni RM1221" - Chembiochem: a European Journal of Chemical Biology 8(6) (2007) 625-631
  

  The complete genome of Campylobacter jejuni strain RM1221 (Penner serotype HS:53) was reported recently and contains a novel capsular polysaccharide (CPS) biosynthesis locus. Cell-surface carbohydrates such as CPS are known to be important for bacterial survival and often contribute to pathogenesis. In this study, we describe the complete structure of the CPS of C. jejuni RM1221, which was determined by using NMR spectroscopy, MS, and chemical methods. The CPS contains 6-deoxy-D-manno-heptose and D-threo-pent-2-ulose (D-xylulose), two monosaccharides that are rarely found in bacterial polysaccharides. The CPS has a regular structure of a linear main chain of trisaccharide repeating units, composed of two α- and one β-6-deoxy-D-manno-heptopyranose residues, which are linked through a phosphodiester linkage. Branching residues of xylulose are incorporated nonstoichiometrically: each trisaccharide repeating unit of the main chain bears no, one, or two xylulose residues. The xylulose glycosidic linkages are extremely acid labile, and it is not clear how they can be preserved under the acidic conditions of the gastrointestinal tract, where Campylobacter resides during infection. We have also shown that the CPS biosynthesis genes of C. jejuni RM1221 are conserved in other C. jejuni strains of the Penner serotype HS:53, including serotype HS:53 reference strain RM3435

  biosynthesis, capsular polysaccharide, Campylobacter jejuni, NMR spectroscopy

  NCBI PubMed ID: 17335095
  Publication DOI: 10.1002/cbic.200600508
  Journal NLM ID: 100937360
  Publisher: Weinheim, Germany: Wiley Interscience
  Correspondence: evguenii.vinogradov@nrc.ca
  Institutions: Institute for Biological Sciences, National Research Council Canada, 100 Sussex Drive, Ottawa, K1A 0R6, Canada
  Methods: 13C NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, mild acid hydrolysis, NMR-1D, genetic methods, CE-ESI-MS
  
   
  
  Campylobacter jejuni RM1221
  CSDB ID 21968 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS

• Article ID: 3407
  Gilbert M, Mandrell RE, Parker CT, Li J, Vinogradov E "Structural analysis of the capsular polysaccharide from Campylobacter jejuni RM1221" - Chembiochem: a European Journal of Chemical Biology 8(6) (2007) 625-631
  

  The complete genome of Campylobacter jejuni strain RM1221 (Penner serotype HS:53) was reported recently and contains a novel capsular polysaccharide (CPS) biosynthesis locus. Cell-surface carbohydrates such as CPS are known to be important for bacterial survival and often contribute to pathogenesis. In this study, we describe the complete structure of the CPS of C. jejuni RM1221, which was determined by using NMR spectroscopy, MS, and chemical methods. The CPS contains 6-deoxy-D-manno-heptose and D-threo-pent-2-ulose (D-xylulose), two monosaccharides that are rarely found in bacterial polysaccharides. The CPS has a regular structure of a linear main chain of trisaccharide repeating units, composed of two α- and one β-6-deoxy-D-manno-heptopyranose residues, which are linked through a phosphodiester linkage. Branching residues of xylulose are incorporated nonstoichiometrically: each trisaccharide repeating unit of the main chain bears no, one, or two xylulose residues. The xylulose glycosidic linkages are extremely acid labile, and it is not clear how they can be preserved under the acidic conditions of the gastrointestinal tract, where Campylobacter resides during infection. We have also shown that the CPS biosynthesis genes of C. jejuni RM1221 are conserved in other C. jejuni strains of the Penner serotype HS:53, including serotype HS:53 reference strain RM3435

  biosynthesis, capsular polysaccharide, Campylobacter jejuni, NMR spectroscopy

  NCBI PubMed ID: 17335095
  Publication DOI: 10.1002/cbic.200600508
  Journal NLM ID: 100937360
  Publisher: Weinheim, Germany: Wiley Interscience
  Correspondence: evguenii.vinogradov@nrc.ca
  Institutions: Institute for Biological Sciences, National Research Council Canada, 100 Sussex Drive, Ottawa, K1A 0R6, Canada
  Methods: 13C NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, mild acid hydrolysis, NMR-1D, genetic methods, CE-ESI-MS
  
   
  
  Campylobacter jejuni RM1221
  CSDB ID 21969 (all data & tools)
• 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/B978-0-12-819475-1.00005-5
  Publisher: 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
  
   
  
  Campylobacter jejuni HS53 (RM1221)
  CSDB ID 7015 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: CDP-D-xylulose
Contained glycoepitopes: IEDB_141494

• Article ID: 4414
  Wang Q, Xu Y, Perepelov AV, Knirel YA, Reeves PR, Shashkov AS, Guo X, Ding P, Feng L "Biochemical characterization of the CDP-D-arabinitol biosynthetic pathway in Streptococcus pneumoniae 17F" - Journal of Bacteriology 194(8) (2012) 1868-1874
  

  Streptococcus pneumoniae is a major human pathogen associated with many diseases worldwide. Capsular polysaccharides (CPSs) are the major virulence factor. The biosynthetic pathway of D-arabinitol, which is present in the CPSs of several S. pneumoniae serotypes, has never been identified. In this study, the genes abpA (previously known as abp1) and abpB (previously known as abp2), which have previously been reported to be responsible for nucleoside diphosphate (NDP)-D-arabinitol (the nucleotide-activated form of D-arabinitol) synthesis, were cloned. The enzyme products were overexpressed, purified, and analyzed for their respective activities. Novel products produced by AbpA- and AbpB-catalyzing reactions were detected by capillary electrophoresis, and the structures of the products were elucidated using electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. As a result, abpA was identified to be a D-xylulose-5-phosphate cytidylyltransferase-encoding gene, responsible for the transfer of CTP to D-xylulose-5-phosphate (D-Xlu-5-P) to form CDP-D-xylulose, and abpB was characterized to be a CDP-D-xylulose reductase-encoding gene, responsible for the conversion of CDP-D-xylulose to CDP-D-arabinitol as the final product. The kinetic parameters of AbpA for the substrates D-Xlu-5-P and CTP and those of AbpB for the substrate CDP-D-xylulose and the cofactors NADH or NADPH were measured, and the effects of temperature, pH, and cations on the two enzymes were analyzed. This study confirmed the involvement of the genes abpA and abpB and their products in the biosynthetic pathway of CDP-D-arabinitol.

  capsular polysaccharides, Streptococcus pneumoniae 17F, CDP-D-arabinitol, biosynthetic pathway

  NCBI PubMed ID: 22328666
  Publication DOI: 10.1128/JB.06487-11
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: Lu Feng
  Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, GLC, genetic methods, enzymatic analysis, RP-HPLC, CE
  
   
  
  Streptococcus pneumoniae 17F
  CSDB ID 27350 (all data & tools)

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Structure type: polymer chemical repeating unit

• Article ID: 5449
  Huddleston JP, Raushel FM "Biosynthesis of GDP-d-glycero-α-d-manno-heptose for the Capsular Polysaccharide of Campylobacter jejuni" - Biochemistry 58(37) (2019) 3893-3902
  

  The capsular polysaccharide (CPS) structure of Campylobacter jejuni contributes to its robust fitness. Many strains contain heptose moieties in their CPS units. The precursor heptose is GDP-d-glycero-α-d-manno-heptose; modifications to the stereochemistry at C3-C6 as well as additions of methyl and phosphoramidate groups lend to the hypervariability of the C. jejuni CPS structures. Synthesis of GDP-d-glycero-α-d-manno-heptose has been described previously, but using enzymes from Aneurinibacillus thermoaerophilus DSM 10155. Here we describe the complete synthesis of GDP-d-glycero-α-d-manno-heptose using enzymes from C. jejuni NTCC 11168: Cj1152 and Cj1423-Cj1425. Our results yield kinetic parameters for these enzymes and outline a successful strategy for milligram-gram scale synthesis of GDP-d-glycero-α-d-manno-heptose. This achievement is critical for the characterization of other carbohydrate tailoring enzymes, which are expected to utilize GDP-d-glycero-α-d-manno-heptose for the biosynthesis of more complex carbohydrates in the CPS of C. jejuni.

  biosynthesis, synthesis, structure, heptose, capsular polysaccharide, Campylobacter jejuni, modification, Enzymes, phosphoramidate, stereochemistry

  NCBI PubMed ID: 31449400
  Publication DOI: 10.1021/acs.biochem.9b00548
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: raushel@tamu.edu
  Institutions: Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
  Methods: 13C NMR, 1H NMR, kinetics assays, 31P NMR, anion-exchange chromatography, MS, genetic methods, HPLC, UV, cloning, bioinformatic analysis, enzymatic synthesis
  
   
  
  Campylobacter jejuni NCTC HS:53
  CSDB ID 783 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS

• Article ID: 5449
  Huddleston JP, Raushel FM "Biosynthesis of GDP-d-glycero-α-d-manno-heptose for the Capsular Polysaccharide of Campylobacter jejuni" - Biochemistry 58(37) (2019) 3893-3902
  

  The capsular polysaccharide (CPS) structure of Campylobacter jejuni contributes to its robust fitness. Many strains contain heptose moieties in their CPS units. The precursor heptose is GDP-d-glycero-α-d-manno-heptose; modifications to the stereochemistry at C3-C6 as well as additions of methyl and phosphoramidate groups lend to the hypervariability of the C. jejuni CPS structures. Synthesis of GDP-d-glycero-α-d-manno-heptose has been described previously, but using enzymes from Aneurinibacillus thermoaerophilus DSM 10155. Here we describe the complete synthesis of GDP-d-glycero-α-d-manno-heptose using enzymes from C. jejuni NTCC 11168: Cj1152 and Cj1423-Cj1425. Our results yield kinetic parameters for these enzymes and outline a successful strategy for milligram-gram scale synthesis of GDP-d-glycero-α-d-manno-heptose. This achievement is critical for the characterization of other carbohydrate tailoring enzymes, which are expected to utilize GDP-d-glycero-α-d-manno-heptose for the biosynthesis of more complex carbohydrates in the CPS of C. jejuni.

  biosynthesis, synthesis, structure, heptose, capsular polysaccharide, Campylobacter jejuni, modification, Enzymes, phosphoramidate, stereochemistry

  NCBI PubMed ID: 31449400
  Publication DOI: 10.1021/acs.biochem.9b00548
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: raushel@tamu.edu
  Institutions: Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
  Methods: 13C NMR, 1H NMR, kinetics assays, 31P NMR, anion-exchange chromatography, MS, genetic methods, HPLC, UV, cloning, bioinformatic analysis, enzymatic synthesis
  
   
  
  Campylobacter jejuni NCTC HS:53
  CSDB ID 783 (all data & tools)

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Structure type: oligomer
Compound class: CPS, cell wall polysaccharide
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,SB_7

• Article ID: 6091
  Kokoulin MS, Romanenko LA, Kuzmich AS, Chernikov OV "Structure of the Cell-Wall-Associated Polysaccharides from the Deep-Sea Marine Bacterium Devosia submarina KMM 9415T" - Marine Drugs 19(12) (2021) 665
  

  Two cell-wall-associated polysaccharides were isolated and purified from the deep-sea marine bacterium Devosia submarina KMM 9415T, purified by ultracentrifugation and enzymatic treatment, separated by chromatographic techniques, and studied by sugar analyses and NMR spectroscopy. The first polysaccharide with a molecular weight of about 20.7 kDa was found to contain D-arabinose, and the following structure of its disaccharide repeating unit was established: →2)-α-D-Araf-(1→5)-α-D-Araf-(1→. The second polysaccharide was shown to consist of D-galactose and a rare component of bacterial glycans-D-xylulose: →3)-α-D-Galp-(1→3)-β-D-Xluf-(1→.

  polysaccharide, Marine bacteria, deep sea, Devosia, xylulose

  NCBI PubMed ID: 34940664
  Publication DOI: 10.3390/md19120665
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, 159/2, Prospect 100 let Vladivostoku, 690022 Vladivostok, Russia, School of Natural Sciences, Far Eastern Federal University, 8, Sukhanova Str., 690950 Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, sugar analysis, mild acid hydrolysis, GC, HPLC, GPC, SEC, enzymatic treatment, ultracentrifugation
  
   
  
  Devosia submarina KMM 9415T
  CSDB ID 9657 (all data & tools)

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Structure type: polymer chemical repeating unit
Compound class: CPS

• Article ID: 6321
  Szymanski CM "Bacterial glycosylation, it's complicated" - Frontiers in Molecular Biosciences 9 (2022) 1015771
  

  Each microbe has the ability to produce a wide variety of sugar structures that includes some combination of glycolipids, glycoproteins, exopolysaccharides and oligosaccharides. For example, bacteria may synthesize lipooligosaccharides or lipopolysaccharides, teichoic and lipoteichoic acids, N- and O-linked glycoproteins, capsular polysaccharides, exopolysaccharides, poly-N-acetylglycosamine polymers, peptidoglycans, osmoregulated periplasmic glucans, trehalose or glycogen, just to name a few of the more broadly distributed carbohydrates that have been studied. The composition of many of these glycans are typically dissimilar from those described in eukaryotes, both in the seemingly endless repertoire of sugars that microbes are capable of synthesizing, and in the unique modifications that are attached to the carbohydrate residues. Furthermore, strain-to-strain differences in the carbohydrate building blocks used to create these glycoconjugates are the norm, and many strains possess additional mechanisms for turning on and off transferases that add specific monosaccharides and/or modifications, exponentially contributing to the structural heterogeneity observed by a single isolate, and preventing any structural generalization at the species level. In the past, a greater proportion of research effort was directed toward characterizing human pathogens rather than commensals or environmental isolates, and historically, the focus was on microbes that were simple to grow in large quantities and straightforward to genetically manipulate. These studies have revealed the complexity that exists among individual strains and have formed a foundation to better understand how other microbes, hosts and environments further transform the glycan composition of a single isolate. These studies also motivate researchers to further explore microbial glycan diversity, particularly as more sensitive analytical instruments and methods are developed to examine microbial populations in situ rather than in large scale from an enriched nutrient flask. This review emphasizes many of these points using the common foodborne pathogen Campylobacter jejuni as the model microbe.

  carbohydrates, Campylobacter jejuni, glycoconjugates, polysaccharides, phase-variation

  NCBI PubMed ID: 36250013
  Publication DOI: 10.3389/fmolb.2022.1015771
  Journal NLM ID: 101653173
  Publisher: Lausanne: Frontiers Media S.A.
  Correspondence: C.M. Szymanski
  Institutions: Department of Microbiology and Complex Carbohydrate Research Center, University of Georgia, Athens, GA, United States, Department of Microbiology and Complex Carbohydrate Research Center, University of Georgia, Athens, GA, United States Christine
  
   
  
  Campylobacter jejuni HS:53
  CSDB ID 8848 (all data & tools)