Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, LPS

• Article ID: 254
  Hatano K, Pier GB "Complex serology and immune response of mice to variant high-molecular-weight O polysaccharide isolated from Pseudomonas aeruginosa serogroup O2 strains" - Infection and Immunity 66(8) (1998) 3719-3726
  

  The O antigen of the Pseudomonas aeruginosa lipopolysaccharide is the optimal target for protective antibodies, but the unusual and complex nature of their sugar substituents has made it difficult to define the range of these structures needed in an effective vaccine. Most clinical isolates of P. aeruginosa can be classified into 10 O-antigen serogroups, but slight chemical differences among O polysaccharides within a serogroup give rise to subtype epitopes. These epitopes could impact the reactivity of O-antigen-specific antibodies, as well as the susceptibility of a target strain to protective, opsonic antibodies. To define parameters of serogroup and subtype-epitope immunogenicity, antigenicity, and surface expression on P. aeruginosa cells, we prepared high-molecular-weight O-polysaccharide vaccines from strains of P. aeruginosa serogroup O2, for which eight structurally variant O antigens expressing six defined subtype epitopes (O2a to O2f) have been identified. A complex pattern of immune responses to these antigens was observed following vaccination of mice. The high-molecular-weight O polysaccharides were generally more immunogenic at low doses (1 and 10 microg) than at a high dose (50 microg) and usually elicited antibodies that opsonized the homologous strain for phagocytic killing. Some of the individual polysaccharides elicited cross-opsonic antibodies to a variable number of strains that express all of the defined serogroup O2 subtype epitopes. Combination into one vaccine of two antigens that individually elicited cross-reactive opsonic antibodies to most members of the O2 serogroup inhibited, instead of enhanced, the production of antibodies broadly reactive with most serogroup O2 subtype strains. Thus, immune responses to P. aeruginosa O antigens may be restricted to a limited range of epitopes on structurally complex O antigens, and combining multiple related antigens into a single vaccine formulation may inhibit the production of those antibodies best able to protect against most P. aeruginosa strains within a given O-antigen serogroup.

  Lipopolysaccharide, Pseudomonas, Pseudomonas aeruginosa, O-polysaccharide, serology, serogroup, immune response

  NCBI PubMed ID: 9673254
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: gpier@channing.harvard.edu
  Institutions: Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115-5804., Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School,Boston, Massachusetts 02115-5804.
  
   
  
  Pseudomonas aeruginosa O2a, Pseudomonas aeruginosa O2c
  CSDB ID 7214 (all data & tools)
• Article ID: 337
  Newton GJ, Daniels C, Burrows LL, Kropinski AM, Clarke AJ, Lam JS "Three-component-mediated serotype conversion in Pseudomonas aeruginosa by bacteriophage D3" - Molecular Microbiology 39(5) (2001) 1237-1247
  

  Bacteriophage D3 is capable of lysogenizing Pseudomonas aeruginosa PAO1 (serotype O5), converting the O-antigen from O5 to O16 and O-acetylating the N-acetylfucosamine moiety. To investigate the mechanism of lysogenic conversion, a 3.6 kb fragment from the D3 genome was isolated capable of mediating serotypic conversion identical to the D3 lysogen strain (AK1380). The PAO1 transformants containing this 3.6 kb of D3 DNA exhibited identical lipopolysaccharide (LPS) banding patterns to serotype O16 in silver-stained SDS-PAGE gels and displayed reactivity to an antibody specific for O-acetyl groups. Further analysis led to the identification of three open reading frames (ORFs) required for serotype conversion: an α-polymerase inhibitor (iap); an O-acetylase (oac); and a β-polymerase (wzyβ). The α-polymerase inhibitor (Iap) is capable of inhibiting the assembly of the serotype-specific O5 B-band LPS and allows the phage-encoded β-polymerase (Wzyβ) to form new β-linked B-band LPS. The D3 phage also alters the LPS by the addition of O-acetyl groups to the FucNAc residue in the O-antigen repeat unit by the action of the D3 O-acetylase (Oac). These three components form a simple yet elegant system by which bacteriophage D3 is capable of altering the surface of P. aeruginosa PAO1

  serotype, Pseudomonas, Pseudomonas aeruginosa, bacteriophage, conversion, serotype conversion

  NCBI PubMed ID: 11251840
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Microbiology, University of Guelph, Guelph, Ontario, N1G 2W1, Canada, The Centre for Infection and Biomaterials Research, Toronto General Hospital, Toronto, Ontario, M5G 2C4, Canada, Department of Microbiology and Immunology, Queen's University, Kingston, Ontario, K7L 3N6, Canada
  Methods: PCR, SDS-PAGE, DNA techniques, Western blotting, quantification of O-acetylation
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 7753 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa O2a,2c,3
  CSDB ID 108475 (all data & tools)
• Article ID: 1833
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK "Structure of Pseudomonas aeruginosa immunotype 3 O-specific polysaccharide: revision of the structure of acetamidino derivative of 2,3-diamino-2,3-dideoxy-D-mannuronic acid" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12(7) (1986) 995-997
  

  O-Specific side chain of P. aeruginosa immunotype 3 lipopolysaccharide is composed of N-acetyl-D-fucosamine (FucNAc), 2,3-diacetamido-2,3-dideoxy-L-guluronic acid (GulN2Ac2A) and 3-acetamidino = 2-acetamido = 2,3 = dideoxy = D-mannuronic acid (ManNAcAmA). The latter sugar is identified on the basis of solvolysis with anhydrous hydrogen fluoride, 13C NMR spectroscopy and fast-atom bombardment mass spectrometry analysis, as well as of reactions of acetamidino function (alkaline hydrolysis to acetamido group and reductive deamination to ethylamino group). Earlier, in the course of investigation of P. aeruginosa O3 lipopolysaccharides, the structure of 1-methyl-2-imidazoline was erroneously ascribed to the acetamidino group. The following structure was established for the repeating unit of immunotype 3 polysaccharide which is identical to P. aeruginosa O3(a),3c polysaccharide: →4)-β-D-ManNAcAmA-(1→4)-α-L-GulN2Ac2A-(1→3)-β-D-FucNac-(1→.

  NCBI PubMed ID: 2429671
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR
  
   
  
  Pseudomonas aeruginosa 3
  CSDB ID 110534 (all data & tools)
• Article ID: 1843
  Elkin YN, Knirel YA, Vinogradov EV, Paramonov NA, Troshkov ML, Aminev "Fast-atom-bombardment mass-spectra of aminooligosaccharides" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1658-1661
  
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: FAB-MS
  
   
  
  Pseudomonas aeruginosa
  CSDB ID 110581 (all data & tools)
• Article ID: 1844
  Knirel YA, Kocharova NA, Vinogradov EV, Paramonov NA, Dmitriev BA, Kochetkov NK, Stanislavsky ES, Kholodkova EV "Antigenic polysaccharides of bacteria. 21. Structure of O-specific polysaccharide chains and serological specificity of lipopolysaccharides of seven Pseudomonas aeruginosa immunotypes" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 13 (1987) 88-96
  

  On mild acid degradation on lipopolysaccharides of seven Pseudomonas aeruginosa immunotypes, O-specific polysaccharides were obtained and their structures established. A peculiar feature of the polysaccharides is the presence of various, mostly acidic, mono- and diaminosugars, many of which have not previously been found in nature. The absence of serological cross-reactions (inhibition of passive haemagglutination) between lipopolysaccharides of seven immunotypes correlates with the absence of any common oligosaccharide fragments in their O-specific chains. The data obtained revealed structural and serological interrelations between O-antigens of seven immunotypes and P. aeruginosa O-serotypes, and showed that immunotypes 1 and 7 should be included into the serological classification scheme as individual O-serotypes.

  NCBI PubMed ID: 2436629
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa O(2a),2c, Pseudomonas aeruginosa 3
  CSDB ID 110592 (all data & tools)
• Article ID: 2409
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Kholodkova EV, Stanislavsky ES "Somatic antigens of Pseudomonas aeruginosa. The structure of O-specific polysaccharide chains of lipopolysaccharides of P. aeruginosa O3 (Lányi), O25 (Wokatsch) and Fisher immunotypes 3 and 7" - European Journal of Biochemistry 167 (1987) 549-561
  

  O-specific polysaccharides, obtained on mild acid degradation of lipopolysacchrides of the serologically related strains Pseudomonas aeruginosa O3 (Lányi classification), O25 (Wokatsch classification) and immunotypes 3 and 7 (Fisher classification), are built up of trisaccharide repeating units involving 2-acetamido-2,6-dideoxy-D-galactose (N-acetyl-D-fucosamine), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid or 2,3-diacetamido-2,3-dideoxy-L-guluronic acid and 3-acetamidino-2-acetamido-2,3-dideoxy-D-mannuronic acid or 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid. Lányi O3(a),3d,3f and Wokatsch O25 polysaccharides contain also O-acetyl groups. On the basis of solvolysis with anhydrous hydrogen fluoride, resulting in trisaccharide fragments with N-acetylfucosamine residue at the reducing terminus, chemical modifications of the acetamidino group (alkaline hydrolysis to the acetamido group or reductive deamination to the ethylamino group), as well as analysis by 1H-NMR (including nuclear Overhauser effect experiments) and 13C-NMR spectroscopy, and fast-atom bombardment mass spectrometry, it was concluded that the repeating units of the polysaccharides have the following structures: (Formula: see text) where HexNAcAmA = α-L-GulNAcAmA (approximately 70%) or β-D-ManNacAMA (approximately 30%). Lányi O3(a),3d,3f polysaccharide involves two types of repeating units, which differ from each other only in the configuration at C-5 of the 3-acetamidino-2-acetamido-2,3-dideoxyuronic acid residue. Lányi O3(a),3c,O3a,3d,3e and Fisher immunotypes 3 and 7 polysaccharides contain, together with the major repeating units shown above, a small proportion of units in which the derivative of α-L-guluronic acid is replaced by the corresponding β-D-manno isomer. The data obtained provide the opportunity to substantiate the serological interrelations between these strains of P. aeruginosa by the presence in the O-specific polysaccharides of common monosaccharides or disaccharide fragments. The distinctions between them stem from the presence or absence of the O-acetyl group, a different configuration of the glycosidic linkage of the N-acetylfucosamine residue and/or a different configuration at C-5 of one or both derivatives of diaminouronic acids.

  NCBI PubMed ID: 3115777
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR, FAB-MS
  
   
  
  Pseudomonas aeruginosa 3a, Pseudomonas aeruginosa 3c, Pseudomonas aeruginosa Lányi
  CSDB ID 123054 (all data & tools)
• Article ID: 3207
  Knirel YA, Bystrova OV, Kocharova NA, Zähringer U, Pier GB "Conserved and variable structural features of the Pseudomonas aeruginosa lipopolysaccharide" - Journal of Endotoxin Research 12(6) (2006) 324-336
  

  The review is devoted to recent progress in the structural elucidation of the lipopolysaccharide of the bacterium Pseudomonas aeruginosa, including O-antigen biological repeats, core oligosaccharide, and lipid A. Data on biosynthesis, genetics and serology of the lipopolysaccharide isolated from various P. aeruginosa O-serogroups are discussed in relation to the chemical structures.

  O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, lipopolysaccharide structure, serologic activity

  NCBI PubMed ID: 17254386
  Publication DOI: 10.1179/096805106X118906
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Brigham and Women’s Hospital, Harvard Medical School, Boston, Massachusetts, USA
  Methods: NMR, chemical methods, MS, serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O2 O(2a),2c, Pseudomonas aeruginosa F3
  CSDB ID 20556 (all data & tools)
• Article ID: 3391
  Kaluzny K, Abeyrathne PD, Lam JS "Coexistence of Two Distinct Versions of O-Antigen Polymerase, Wzy-Alpha and Wzy-Beta, in Pseudomonas aeruginosa Serogroup O2 and Their Contributions to Cell Surface Diversity" - Journal of Bacteriology 189(11) (2007) 4141-4152
  

  Assembly of B-band LPS in Pseudomonas aeruginosa follows a Wzy-dependent pathway, requiring the O-antigen polymerase Wzy, and other proteins. The peptide sequences of the wzyα product from strains of serotypes O2, O5, and O16 are identical; but the O-units in O5 are α-glycosidic-linked, while those in O2 and O16 are β-linked. We hypothesized that a derivative of the D3 bacteriophage wzyβ is present in the chromosomes of O2 and O16, and that this gene is responsible for the β-linkage. By a combination of PCR and primer walking, wzyβ of both serotypes have been amplified and cloned. Both are identical, but only share 87.42% sequence identity with their xenolog in D3. A chromosomal knockout mutant of O16 wzyβ was made and it produces rough LPS devoid of B-band O antigen. The cloned wzyβ is capable of complementing the O16 wzyβ mutant, as well as cross-complementing a wzyα knockout mutant. However, in the latter case, the restored O-antigen was β-linked. Using RT-PCR, we showed that wzyα was transcribed in O2 and O16 strains and was functional since both of these genes could complement the wzyα mutant of O5. With the co-existence of wzyα and wzyβ in O2 and O16 and the B-band O polysaccharides in these being β-linked, we hypothesized that iap, an inhibitor of alpha-polymerase gene, must be present in these serotypes. Indeed, through PCR, TOPO cloning and nucleotide sequencing results, we verified the presence of iap in both O2 and O16 serotypes

  serotype, Pseudomonas aeruginosa, O-polysaccharide, serogroup, sequencing, O-antigen polymerase, rough LPS

  NCBI PubMed ID: 17384183
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: jlam@uoguelph.ca
  Institutions: University of Guelph, Department of Molecular and Cellular Biology, Guelph, Ontario, Canada N1G 2W1
  Methods: serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 21549 (all data & tools)
• Article ID: 3711
  King JD, Kocincova D, Westman EL, Lam JS "Lipopolysaccharide biosynthesis in Pseudomonas aeruginosa" - Innate Immunity 15(5) (2009) 261-312
  

  Pseudomonas aeruginosa causes serious nosocomial infections, and an important virulence factor produced by this organism is lipopolysaccharide (LPS). This review summarizes knowledge about biosynthesis of all three structural domains of LPS - lipid A, core oligosaccharide, and O polysaccharides. In addition, based on similarities with other bacterial species, this review proposes new hypothetical pathways for unstudied steps in the biosynthesis of P. aeruginosa LPS. Lipid A biosynthesis is discussed in relation to Escherichia coli and Salmonella, and the biosyntheses of core sugar precursors and core oligosaccharide are summarised. Pseudomonas aeruginosa attaches a Common Polysaccharide Antigen and O-Specific Antigen polysaccharides to lipid A-core. Both forms of O polysaccharide are discussed with respect to their independent synthesis mechanisms. Recent advances in understanding O-polysaccharide biosynthesis since the last major review on this subject, published nearly a decade ago, are highlighted. Since P. aeruginosa O polysaccharides contain unusual sugars, sugar-nucleotide biosynthesis pathways are reviewed in detail. Knowledge derived from detailed studies in the O5, O6 and O11 serotypes is applied to predict biosynthesis pathways of sugars in poorly-studied serotypes, especially O1, O4, and O13/O14. Although further work is required, a full understanding of LPS biosynthesis in P. aeruginosa is almost within reach.

  Lipopolysaccharide, core, O-antigen, Pseudomonas aeruginosa, lipid A

  NCBI PubMed ID: 19710102
  Publication DOI: 10.1177/1753425909106436
  Journal NLM ID: 101469670
  Publisher: Sage Publications
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 24028 (all data & tools)
• Article ID: 4062
  Lam JS, Taylor VL, Islam ST, Hao Y, Kocincova D "Genetic and Functional Diversity of Pseudomonas aeruginosa Lipopolysaccharide" - Frontiers in Microbiology 2 (2011) 118
  

  Lipopolysccharide (LPS) is an integral component of the Pseudomonas aeruginosa cell envelope, occupying the outer leaflet of the outer membrane in this Gram-negative opportunistic pathogen. It is important for bacterium-host interactions and has been shown to be a major virulence factor for this organism. Structurally, P. aeruginosa LPS is composed of three domains, namely, lipid A, core oligosaccharide, and the distal O antigen (O-Ag). Most P. aeruginosa strains produce two distinct forms of O-Ag, one a homopolymer of D-rhamnose that is a common polysaccharide antigen (CPA, formerly termed A band), and the other a heteropolymer of three to five distinct (and often unique dideoxy) sugars in its repeat units, known as O-specific antigen (OSA, formerly termed B band). Compositional differences in the O units among the OSA from different strains form the basis of the International Antigenic Typing Scheme for classification via serotyping of different strains of P. aeruginosa. The focus of this review is to provide state-of-the-art knowledge on the genetic and resultant functional diversity of LPS produced by P. aeruginosa. The underlying factors contributing to this diversity will be thoroughly discussed and presented in the context of its contributions to host-pathogen interactions and the control/prevention of infection.

  Lipopolysaccharide, biosynthesis, virulence, serotyping, bacteriophage, motility, seroconversion, nucleotide sugars

  NCBI PubMed ID: 21687428
  Publication DOI: 10.3389/fmicb.2011.00118
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 26860 (all data & tools)
• Article ID: 4684
  Islam ST, Lam JS "Synthesis of bacterial polysaccharides via the Wzx/Wzy-dependent pathway" - Canadian Journal of Microbiology 60(11) (2014) 697-716
  

  The surfaces of bacteria mediate a multitude of functions in the environment and in an infected host, including adhesion to both biotic and abiotic substrata, motility, immune system interaction and (or) activation, biofilm formation, and cell-cell communication, with many of these features directly influenced by cell-surface glycans. In both Gram-negative and Gram-positive bacteria, the majority of cell-surface polysaccharides are produced via the Wzx/Wzy-dependent assembly pathway; these glycans include heteropolymeric O-antigen, enterobacterial common antigen, exopolysaccharide, spore coat, and capsule in diverse bacteria. The key components of this assembly pathway are the integral inner membrane Wzx flippase, Wzy polymerase, and Wzz chain-length regulator proteins, which until recently have resisted detailed structural and functional characterization. In this review, we have provided a comprehensive synthesis of the latest structural and mechanistic data for each protein, as well as an examination of substrate specificity for each assembly step and complex formation between the constituent proteins. To complement the unprecedented explosion of genomic-sequencing data for bacteria, we have also highlighted both classical and state-of-the-art methods by which encoded Wzx, Wzy, and Wzz proteins can be reliably identified and annotated, using the model Gram-negative bacterium Pseudomonas aeruginosa as an example data set. Lastly, we outline future avenues of research, with the aim of stimulating researchers to take the next steps in investigating the function of, and interplay between, the constituents of this widespread assembly scheme.

  Membrane Proteins, lipopolysaccharide (LPS), Wzx flippase, Wzy polymerase, Wzz polysaccharide copolymerase

  NCBI PubMed ID: 25358682
  Publication DOI: 10.1139/cjm-2014-0595
  Journal NLM ID: 0372707
  Publisher: National Research Council of Canada
  Correspondence: sislam@imm.cnrs.fr; jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON N1G 2W1, Canada
  Methods: SDS-PAGE, genetic methods, cloning
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 30276 (all data & tools)
• Article ID: 4932
  Taylor VL, Hoage JF, Thrane SW, Huszczynski SM, Jelsbak L, Lam JS "A Bacteriophage-Acquired O-Antigen Polymerase (Wzyb) from P. aeruginosa Serotype O16 Performs a Varied Mechanism Compared to Its Cognate Wzya" - Frontiers in Microbiology 7 (2016) 393
  

  Pseudomonas aeruginosa is a Gram-negative bacterium that produces highly varied lipopolysaccharide (LPS) structures. The O antigen (O-Ag) in the LPS is synthesized through the Wzx/Wzy-dependent pathway where lipid-linked O-Ag repeats are polymerized by Wzy. Horizontal-gene transfer has been associated with O-Ag diversity. The O-Ag present on the surface of serotypes O5 and O16, differ in the intra-molecular bonds, alpha and beta, respectively; the latter arose from the action of three genes in a serotype converting unit acquired from bacteriophage D3, including a beta-polymerase (Wzyβ). To further our understanding of O-polymerases, the inner membrane (IM) topology of Wzyβ was determined using a dual phoA-lacZα reporter system wherein random 3' gene truncations were localized to specific loci with respect to the IM by normalized reporter activities as determined through the ratio of alkaline phosphatase activity to β-galactosidase activity. The topology of Wzyβ developed through this approach was shown to contain two predominant periplasmic loops, PL3 (containing an RX10G motif) and PL4 (having an O-Ag ligase superfamily motif), associated with inverting glycosyltransferase reaction. Through site-directed mutagenesis and complementation assays, residues Arg(254), Arg(270), Arg(272), and His(300) were found to be essential for Wzyβ function. Additionally, like-charge substitutions, R254K and R270K, could not complement the wzyβ knockout, highlighting the essential guanidium side group of Arg residues. The O-Ag ligase domain is conserved among heterologous Wzy proteins that produce β-linked O-Ag repeat units. Taking advantage of the recently obtained whole-genome sequence of serotype O16 a candidate promoter was identified. Wzyβ under its native promoter was integrated in the PAO1 genome, which resulted in simultaneous production of α- and β-linked O-Ag. These observations established that members of Wzy-like family consistently exhibit a dual-periplasmic loops topology, and identifies motifs that are plausible to be involved in enzymatic activities. Based on these results, the phage-derived Wzyβ utilizes a different reaction mechanism in the P. aeruginosa host to avoid self-inhibition during serotype conversion.

  Lipopolysaccharide, serotype, Pseudomonas aeruginosa, glycosyltransferase, bacteriophage, O-antigen biosynthesis, polymerase

  NCBI PubMed ID: 27065964
  Publication DOI: 10.3389/fmicb.2016.00393
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada, Department of Systems Biology, Technical University of Denmark Kongens Lyngby, Denmark
  Methods: PCR, SDS-PAGE, Western blotting, genetic methods, enzymatic assay
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 11742 (all data & tools)
• Article ID: 5760
  Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" - Molecular Immunology 120 (2020) 74-82
  

  To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.

  cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen

  NCBI PubMed ID: 32087569
  Publication DOI: 10.1016/j.molimm.2020.02.005
  Journal NLM ID: 7905289
  Publisher: Elsevier
  Correspondence: professorbovin@yandex.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
  Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
  
   
  
  Pseudomonas aeruginosa O2ac, Pseudomonas aeruginosa F3
  CSDB ID 3931 (all data & tools)
• 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: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: 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
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 9102 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 254
  Hatano K, Pier GB "Complex serology and immune response of mice to variant high-molecular-weight O polysaccharide isolated from Pseudomonas aeruginosa serogroup O2 strains" - Infection and Immunity 66(8) (1998) 3719-3726
  

  The O antigen of the Pseudomonas aeruginosa lipopolysaccharide is the optimal target for protective antibodies, but the unusual and complex nature of their sugar substituents has made it difficult to define the range of these structures needed in an effective vaccine. Most clinical isolates of P. aeruginosa can be classified into 10 O-antigen serogroups, but slight chemical differences among O polysaccharides within a serogroup give rise to subtype epitopes. These epitopes could impact the reactivity of O-antigen-specific antibodies, as well as the susceptibility of a target strain to protective, opsonic antibodies. To define parameters of serogroup and subtype-epitope immunogenicity, antigenicity, and surface expression on P. aeruginosa cells, we prepared high-molecular-weight O-polysaccharide vaccines from strains of P. aeruginosa serogroup O2, for which eight structurally variant O antigens expressing six defined subtype epitopes (O2a to O2f) have been identified. A complex pattern of immune responses to these antigens was observed following vaccination of mice. The high-molecular-weight O polysaccharides were generally more immunogenic at low doses (1 and 10 microg) than at a high dose (50 microg) and usually elicited antibodies that opsonized the homologous strain for phagocytic killing. Some of the individual polysaccharides elicited cross-opsonic antibodies to a variable number of strains that express all of the defined serogroup O2 subtype epitopes. Combination into one vaccine of two antigens that individually elicited cross-reactive opsonic antibodies to most members of the O2 serogroup inhibited, instead of enhanced, the production of antibodies broadly reactive with most serogroup O2 subtype strains. Thus, immune responses to P. aeruginosa O antigens may be restricted to a limited range of epitopes on structurally complex O antigens, and combining multiple related antigens into a single vaccine formulation may inhibit the production of those antibodies best able to protect against most P. aeruginosa strains within a given O-antigen serogroup.

  Lipopolysaccharide, Pseudomonas, Pseudomonas aeruginosa, O-polysaccharide, serology, serogroup, immune response

  NCBI PubMed ID: 9673254
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: gpier@channing.harvard.edu
  Institutions: Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115-5804., Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School,Boston, Massachusetts 02115-5804.
  
   
  
  Pseudomonas aeruginosa O2a, Pseudomonas aeruginosa O2d, Pseudomonas aeruginosa O2e
  CSDB ID 7216 (all data & tools)
• Article ID: 1412
  de Kievit TR, Staples T, Lam JS "Pseudomonas aeruginosa rfc genes of serotypes O2 and O5 could complement O-polymerase-deficient semi-rough mutants of either serotype" - FEMS Microbiology Reviews 147(2) (1997) 251-257
  

  Using a gene-replacement strategy and a mutated copy of the Pseudomonas aeruginosa O5 rfc gene, we were able to generate a rfc mutant in P. aeruginosa serotype O2. This mutant, which exhibits the semi-rough (SR) LPS phenotype, was used to isolate the O2 rfc gene. Mobilization of the O2 and O5 rfc genes into SR mutants of the heterologous serotype resulted in 'cross-polymerization' of O-repeat units, indicating that the genes are functionally exchangeable. Analysis of the nucleotide sequence of the rfc genes revealed that the two Rfc proteins are identical. The results of this study have enabled us to propose the linkage catalyzed by the O5 O-polymerase enzyme.

  Lipopolysaccharide, LPS, gene, serotype, Pseudomonas, Pseudomonas aeruginosa, mutant, mutants, Serotypes, O-antigen polymerase, rfc, complement, semirough

  NCBI PubMed ID: 9119201
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: jlam@micro.uoguelph.ca
  Institutions: Department of Microbiology, University of Guelph, Guelph, Canada
  
   
  
  Pseudomonas aeruginosa O2
  CSDB ID 6565 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa O2a,2d
  CSDB ID 108481 (all data & tools)
• Article ID: 2409
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Kholodkova EV, Stanislavsky ES "Somatic antigens of Pseudomonas aeruginosa. The structure of O-specific polysaccharide chains of lipopolysaccharides of P. aeruginosa O3 (Lányi), O25 (Wokatsch) and Fisher immunotypes 3 and 7" - European Journal of Biochemistry 167 (1987) 549-561
  

  O-specific polysaccharides, obtained on mild acid degradation of lipopolysacchrides of the serologically related strains Pseudomonas aeruginosa O3 (Lányi classification), O25 (Wokatsch classification) and immunotypes 3 and 7 (Fisher classification), are built up of trisaccharide repeating units involving 2-acetamido-2,6-dideoxy-D-galactose (N-acetyl-D-fucosamine), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid or 2,3-diacetamido-2,3-dideoxy-L-guluronic acid and 3-acetamidino-2-acetamido-2,3-dideoxy-D-mannuronic acid or 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid. Lányi O3(a),3d,3f and Wokatsch O25 polysaccharides contain also O-acetyl groups. On the basis of solvolysis with anhydrous hydrogen fluoride, resulting in trisaccharide fragments with N-acetylfucosamine residue at the reducing terminus, chemical modifications of the acetamidino group (alkaline hydrolysis to the acetamido group or reductive deamination to the ethylamino group), as well as analysis by 1H-NMR (including nuclear Overhauser effect experiments) and 13C-NMR spectroscopy, and fast-atom bombardment mass spectrometry, it was concluded that the repeating units of the polysaccharides have the following structures: (Formula: see text) where HexNAcAmA = α-L-GulNAcAmA (approximately 70%) or β-D-ManNacAMA (approximately 30%). Lányi O3(a),3d,3f polysaccharide involves two types of repeating units, which differ from each other only in the configuration at C-5 of the 3-acetamidino-2-acetamido-2,3-dideoxyuronic acid residue. Lányi O3(a),3c,O3a,3d,3e and Fisher immunotypes 3 and 7 polysaccharides contain, together with the major repeating units shown above, a small proportion of units in which the derivative of α-L-guluronic acid is replaced by the corresponding β-D-manno isomer. The data obtained provide the opportunity to substantiate the serological interrelations between these strains of P. aeruginosa by the presence in the O-specific polysaccharides of common monosaccharides or disaccharide fragments. The distinctions between them stem from the presence or absence of the O-acetyl group, a different configuration of the glycosidic linkage of the N-acetylfucosamine residue and/or a different configuration at C-5 of one or both derivatives of diaminouronic acids.

  NCBI PubMed ID: 3115777
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR, FAB-MS
  
   
  
  Pseudomonas aeruginosa 3a, Pseudomonas aeruginosa 3d, Pseudomonas aeruginosa 3e, Pseudomonas aeruginosa Lányi
  CSDB ID 123055 (all data & tools)
• Article ID: 3207
  Knirel YA, Bystrova OV, Kocharova NA, Zähringer U, Pier GB "Conserved and variable structural features of the Pseudomonas aeruginosa lipopolysaccharide" - Journal of Endotoxin Research 12(6) (2006) 324-336
  

  The review is devoted to recent progress in the structural elucidation of the lipopolysaccharide of the bacterium Pseudomonas aeruginosa, including O-antigen biological repeats, core oligosaccharide, and lipid A. Data on biosynthesis, genetics and serology of the lipopolysaccharide isolated from various P. aeruginosa O-serogroups are discussed in relation to the chemical structures.

  O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, lipopolysaccharide structure, serologic activity

  NCBI PubMed ID: 17254386
  Publication DOI: 10.1179/096805106X118906
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Brigham and Women’s Hospital, Harvard Medical School, Boston, Massachusetts, USA
  Methods: NMR, chemical methods, MS, serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O5 O2a,2d,2e
  CSDB ID 20558 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 254
  Hatano K, Pier GB "Complex serology and immune response of mice to variant high-molecular-weight O polysaccharide isolated from Pseudomonas aeruginosa serogroup O2 strains" - Infection and Immunity 66(8) (1998) 3719-3726
  

  The O antigen of the Pseudomonas aeruginosa lipopolysaccharide is the optimal target for protective antibodies, but the unusual and complex nature of their sugar substituents has made it difficult to define the range of these structures needed in an effective vaccine. Most clinical isolates of P. aeruginosa can be classified into 10 O-antigen serogroups, but slight chemical differences among O polysaccharides within a serogroup give rise to subtype epitopes. These epitopes could impact the reactivity of O-antigen-specific antibodies, as well as the susceptibility of a target strain to protective, opsonic antibodies. To define parameters of serogroup and subtype-epitope immunogenicity, antigenicity, and surface expression on P. aeruginosa cells, we prepared high-molecular-weight O-polysaccharide vaccines from strains of P. aeruginosa serogroup O2, for which eight structurally variant O antigens expressing six defined subtype epitopes (O2a to O2f) have been identified. A complex pattern of immune responses to these antigens was observed following vaccination of mice. The high-molecular-weight O polysaccharides were generally more immunogenic at low doses (1 and 10 microg) than at a high dose (50 microg) and usually elicited antibodies that opsonized the homologous strain for phagocytic killing. Some of the individual polysaccharides elicited cross-opsonic antibodies to a variable number of strains that express all of the defined serogroup O2 subtype epitopes. Combination into one vaccine of two antigens that individually elicited cross-reactive opsonic antibodies to most members of the O2 serogroup inhibited, instead of enhanced, the production of antibodies broadly reactive with most serogroup O2 subtype strains. Thus, immune responses to P. aeruginosa O antigens may be restricted to a limited range of epitopes on structurally complex O antigens, and combining multiple related antigens into a single vaccine formulation may inhibit the production of those antibodies best able to protect against most P. aeruginosa strains within a given O-antigen serogroup.

  Lipopolysaccharide, Pseudomonas, Pseudomonas aeruginosa, O-polysaccharide, serology, serogroup, immune response

  NCBI PubMed ID: 9673254
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: gpier@channing.harvard.edu
  Institutions: Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115-5804., Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School,Boston, Massachusetts 02115-5804.
  
   
  
  Pseudomonas aeruginosa O2a, Pseudomonas aeruginosa O2d, Pseudomonas aeruginosa O2f
  CSDB ID 7218 (all data & tools)
• Article ID: 337
  Newton GJ, Daniels C, Burrows LL, Kropinski AM, Clarke AJ, Lam JS "Three-component-mediated serotype conversion in Pseudomonas aeruginosa by bacteriophage D3" - Molecular Microbiology 39(5) (2001) 1237-1247
  

  Bacteriophage D3 is capable of lysogenizing Pseudomonas aeruginosa PAO1 (serotype O5), converting the O-antigen from O5 to O16 and O-acetylating the N-acetylfucosamine moiety. To investigate the mechanism of lysogenic conversion, a 3.6 kb fragment from the D3 genome was isolated capable of mediating serotypic conversion identical to the D3 lysogen strain (AK1380). The PAO1 transformants containing this 3.6 kb of D3 DNA exhibited identical lipopolysaccharide (LPS) banding patterns to serotype O16 in silver-stained SDS-PAGE gels and displayed reactivity to an antibody specific for O-acetyl groups. Further analysis led to the identification of three open reading frames (ORFs) required for serotype conversion: an α-polymerase inhibitor (iap); an O-acetylase (oac); and a β-polymerase (wzyβ). The α-polymerase inhibitor (Iap) is capable of inhibiting the assembly of the serotype-specific O5 B-band LPS and allows the phage-encoded β-polymerase (Wzyβ) to form new β-linked B-band LPS. The D3 phage also alters the LPS by the addition of O-acetyl groups to the FucNAc residue in the O-antigen repeat unit by the action of the D3 O-acetylase (Oac). These three components form a simple yet elegant system by which bacteriophage D3 is capable of altering the surface of P. aeruginosa PAO1

  serotype, Pseudomonas, Pseudomonas aeruginosa, bacteriophage, conversion, serotype conversion

  NCBI PubMed ID: 11251840
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Microbiology, University of Guelph, Guelph, Ontario, N1G 2W1, Canada, The Centre for Infection and Biomaterials Research, Toronto General Hospital, Toronto, Ontario, M5G 2C4, Canada, Department of Microbiology and Immunology, Queen's University, Kingston, Ontario, K7L 3N6, Canada
  Methods: PCR, SDS-PAGE, DNA techniques, Western blotting, quantification of O-acetylation
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 7837 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa O2a,2d,2f
  CSDB ID 108476 (all data & tools)
• Article ID: 1842
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES "Antigenic polysaccharides of bacteria. 20. Structure of the O-specific polysaccharide chain of P. aeruginosa O3(a),3d,3f (Lányi) lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1649-1657
  

  Mild acid degradation of lipopolysaccharide from Pseudomonas aeruginosa O(3a), 3d, 3f (Lányi classification) afforded O-specific polysaccharide containing N-acetyl-D-fucosamine, 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid, 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic and D-mannuronic acid as well as O-acetyl groups. On the basis of O-deacetylation, selective cleavage with anhydrous fluoride, chemical transformation of the oligosaccharides obtained (hydrolysis or reductive deamination of the acetamidino group into acetamido or ethylamino group, respectively) and analysis by 13C NMR spectroscopy, it was concluded that the polysaccharide is built up mainly by trisaccharide repeating units of types A and B in the ratio approximately 2:1: (Formula: see text). The units of both types most probably enter the same polymeric chain. If so, such a hybrid structure can be accounted for by incompleteness of epimerization at C5 of the acetamidino derivative of mannuronic acid at the polymer level in the course of biosynthesis of this polysaccharide.

  NCBI PubMed ID: 2434103
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR
  
   
  
  Pseudomonas aeruginosa O(3a),3d,3f
  CSDB ID 110577 (all data & tools)
• Article ID: 3207
  Knirel YA, Bystrova OV, Kocharova NA, Zähringer U, Pier GB "Conserved and variable structural features of the Pseudomonas aeruginosa lipopolysaccharide" - Journal of Endotoxin Research 12(6) (2006) 324-336
  

  The review is devoted to recent progress in the structural elucidation of the lipopolysaccharide of the bacterium Pseudomonas aeruginosa, including O-antigen biological repeats, core oligosaccharide, and lipid A. Data on biosynthesis, genetics and serology of the lipopolysaccharide isolated from various P. aeruginosa O-serogroups are discussed in relation to the chemical structures.

  O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, lipopolysaccharide structure, serologic activity

  NCBI PubMed ID: 17254386
  Publication DOI: 10.1179/096805106X118906
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Brigham and Women’s Hospital, Harvard Medical School, Boston, Massachusetts, USA
  Methods: NMR, chemical methods, MS, serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O20 O2a,2d,2f
  CSDB ID 20559 (all data & tools)
• Article ID: 3391
  Kaluzny K, Abeyrathne PD, Lam JS "Coexistence of Two Distinct Versions of O-Antigen Polymerase, Wzy-Alpha and Wzy-Beta, in Pseudomonas aeruginosa Serogroup O2 and Their Contributions to Cell Surface Diversity" - Journal of Bacteriology 189(11) (2007) 4141-4152
  

  Assembly of B-band LPS in Pseudomonas aeruginosa follows a Wzy-dependent pathway, requiring the O-antigen polymerase Wzy, and other proteins. The peptide sequences of the wzyα product from strains of serotypes O2, O5, and O16 are identical; but the O-units in O5 are α-glycosidic-linked, while those in O2 and O16 are β-linked. We hypothesized that a derivative of the D3 bacteriophage wzyβ is present in the chromosomes of O2 and O16, and that this gene is responsible for the β-linkage. By a combination of PCR and primer walking, wzyβ of both serotypes have been amplified and cloned. Both are identical, but only share 87.42% sequence identity with their xenolog in D3. A chromosomal knockout mutant of O16 wzyβ was made and it produces rough LPS devoid of B-band O antigen. The cloned wzyβ is capable of complementing the O16 wzyβ mutant, as well as cross-complementing a wzyα knockout mutant. However, in the latter case, the restored O-antigen was β-linked. Using RT-PCR, we showed that wzyα was transcribed in O2 and O16 strains and was functional since both of these genes could complement the wzyα mutant of O5. With the co-existence of wzyα and wzyβ in O2 and O16 and the B-band O polysaccharides in these being β-linked, we hypothesized that iap, an inhibitor of alpha-polymerase gene, must be present in these serotypes. Indeed, through PCR, TOPO cloning and nucleotide sequencing results, we verified the presence of iap in both O2 and O16 serotypes

  serotype, Pseudomonas aeruginosa, O-polysaccharide, serogroup, sequencing, O-antigen polymerase, rough LPS

  NCBI PubMed ID: 17384183
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: jlam@uoguelph.ca
  Institutions: University of Guelph, Department of Molecular and Cellular Biology, Guelph, Ontario, Canada N1G 2W1
  Methods: serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 21927 (all data & tools)
• Article ID: 4062
  Lam JS, Taylor VL, Islam ST, Hao Y, Kocincova D "Genetic and Functional Diversity of Pseudomonas aeruginosa Lipopolysaccharide" - Frontiers in Microbiology 2 (2011) 118
  

  Lipopolysccharide (LPS) is an integral component of the Pseudomonas aeruginosa cell envelope, occupying the outer leaflet of the outer membrane in this Gram-negative opportunistic pathogen. It is important for bacterium-host interactions and has been shown to be a major virulence factor for this organism. Structurally, P. aeruginosa LPS is composed of three domains, namely, lipid A, core oligosaccharide, and the distal O antigen (O-Ag). Most P. aeruginosa strains produce two distinct forms of O-Ag, one a homopolymer of D-rhamnose that is a common polysaccharide antigen (CPA, formerly termed A band), and the other a heteropolymer of three to five distinct (and often unique dideoxy) sugars in its repeat units, known as O-specific antigen (OSA, formerly termed B band). Compositional differences in the O units among the OSA from different strains form the basis of the International Antigenic Typing Scheme for classification via serotyping of different strains of P. aeruginosa. The focus of this review is to provide state-of-the-art knowledge on the genetic and resultant functional diversity of LPS produced by P. aeruginosa. The underlying factors contributing to this diversity will be thoroughly discussed and presented in the context of its contributions to host-pathogen interactions and the control/prevention of infection.

  Lipopolysaccharide, biosynthesis, virulence, serotyping, bacteriophage, motility, seroconversion, nucleotide sugars

  NCBI PubMed ID: 21687428
  Publication DOI: 10.3389/fmicb.2011.00118
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 26864 (all data & tools)
• Article ID: 4684
  Islam ST, Lam JS "Synthesis of bacterial polysaccharides via the Wzx/Wzy-dependent pathway" - Canadian Journal of Microbiology 60(11) (2014) 697-716
  

  The surfaces of bacteria mediate a multitude of functions in the environment and in an infected host, including adhesion to both biotic and abiotic substrata, motility, immune system interaction and (or) activation, biofilm formation, and cell-cell communication, with many of these features directly influenced by cell-surface glycans. In both Gram-negative and Gram-positive bacteria, the majority of cell-surface polysaccharides are produced via the Wzx/Wzy-dependent assembly pathway; these glycans include heteropolymeric O-antigen, enterobacterial common antigen, exopolysaccharide, spore coat, and capsule in diverse bacteria. The key components of this assembly pathway are the integral inner membrane Wzx flippase, Wzy polymerase, and Wzz chain-length regulator proteins, which until recently have resisted detailed structural and functional characterization. In this review, we have provided a comprehensive synthesis of the latest structural and mechanistic data for each protein, as well as an examination of substrate specificity for each assembly step and complex formation between the constituent proteins. To complement the unprecedented explosion of genomic-sequencing data for bacteria, we have also highlighted both classical and state-of-the-art methods by which encoded Wzx, Wzy, and Wzz proteins can be reliably identified and annotated, using the model Gram-negative bacterium Pseudomonas aeruginosa as an example data set. Lastly, we outline future avenues of research, with the aim of stimulating researchers to take the next steps in investigating the function of, and interplay between, the constituents of this widespread assembly scheme.

  Membrane Proteins, lipopolysaccharide (LPS), Wzx flippase, Wzy polymerase, Wzz polysaccharide copolymerase

  NCBI PubMed ID: 25358682
  Publication DOI: 10.1139/cjm-2014-0595
  Journal NLM ID: 0372707
  Publisher: National Research Council of Canada
  Correspondence: sislam@imm.cnrs.fr; jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON N1G 2W1, Canada
  Methods: SDS-PAGE, genetic methods, cloning
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 30280 (all data & tools)
• Article ID: 4932
  Taylor VL, Hoage JF, Thrane SW, Huszczynski SM, Jelsbak L, Lam JS "A Bacteriophage-Acquired O-Antigen Polymerase (Wzyb) from P. aeruginosa Serotype O16 Performs a Varied Mechanism Compared to Its Cognate Wzya" - Frontiers in Microbiology 7 (2016) 393
  

  Pseudomonas aeruginosa is a Gram-negative bacterium that produces highly varied lipopolysaccharide (LPS) structures. The O antigen (O-Ag) in the LPS is synthesized through the Wzx/Wzy-dependent pathway where lipid-linked O-Ag repeats are polymerized by Wzy. Horizontal-gene transfer has been associated with O-Ag diversity. The O-Ag present on the surface of serotypes O5 and O16, differ in the intra-molecular bonds, alpha and beta, respectively; the latter arose from the action of three genes in a serotype converting unit acquired from bacteriophage D3, including a beta-polymerase (Wzyβ). To further our understanding of O-polymerases, the inner membrane (IM) topology of Wzyβ was determined using a dual phoA-lacZα reporter system wherein random 3' gene truncations were localized to specific loci with respect to the IM by normalized reporter activities as determined through the ratio of alkaline phosphatase activity to β-galactosidase activity. The topology of Wzyβ developed through this approach was shown to contain two predominant periplasmic loops, PL3 (containing an RX10G motif) and PL4 (having an O-Ag ligase superfamily motif), associated with inverting glycosyltransferase reaction. Through site-directed mutagenesis and complementation assays, residues Arg(254), Arg(270), Arg(272), and His(300) were found to be essential for Wzyβ function. Additionally, like-charge substitutions, R254K and R270K, could not complement the wzyβ knockout, highlighting the essential guanidium side group of Arg residues. The O-Ag ligase domain is conserved among heterologous Wzy proteins that produce β-linked O-Ag repeat units. Taking advantage of the recently obtained whole-genome sequence of serotype O16 a candidate promoter was identified. Wzyβ under its native promoter was integrated in the PAO1 genome, which resulted in simultaneous production of α- and β-linked O-Ag. These observations established that members of Wzy-like family consistently exhibit a dual-periplasmic loops topology, and identifies motifs that are plausible to be involved in enzymatic activities. Based on these results, the phage-derived Wzyβ utilizes a different reaction mechanism in the P. aeruginosa host to avoid self-inhibition during serotype conversion.

  Lipopolysaccharide, serotype, Pseudomonas aeruginosa, glycosyltransferase, bacteriophage, O-antigen biosynthesis, polymerase

  NCBI PubMed ID: 27065964
  Publication DOI: 10.3389/fmicb.2016.00393
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada, Department of Systems Biology, Technical University of Denmark Kongens Lyngby, Denmark
  Methods: PCR, SDS-PAGE, Western blotting, genetic methods, enzymatic assay
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 11744 (all data & tools)
• 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: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: 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
  
   
  
  Pseudomonas aeruginosa O20
  CSDB ID 9108 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 254
  Hatano K, Pier GB "Complex serology and immune response of mice to variant high-molecular-weight O polysaccharide isolated from Pseudomonas aeruginosa serogroup O2 strains" - Infection and Immunity 66(8) (1998) 3719-3726
  

  The O antigen of the Pseudomonas aeruginosa lipopolysaccharide is the optimal target for protective antibodies, but the unusual and complex nature of their sugar substituents has made it difficult to define the range of these structures needed in an effective vaccine. Most clinical isolates of P. aeruginosa can be classified into 10 O-antigen serogroups, but slight chemical differences among O polysaccharides within a serogroup give rise to subtype epitopes. These epitopes could impact the reactivity of O-antigen-specific antibodies, as well as the susceptibility of a target strain to protective, opsonic antibodies. To define parameters of serogroup and subtype-epitope immunogenicity, antigenicity, and surface expression on P. aeruginosa cells, we prepared high-molecular-weight O-polysaccharide vaccines from strains of P. aeruginosa serogroup O2, for which eight structurally variant O antigens expressing six defined subtype epitopes (O2a to O2f) have been identified. A complex pattern of immune responses to these antigens was observed following vaccination of mice. The high-molecular-weight O polysaccharides were generally more immunogenic at low doses (1 and 10 microg) than at a high dose (50 microg) and usually elicited antibodies that opsonized the homologous strain for phagocytic killing. Some of the individual polysaccharides elicited cross-opsonic antibodies to a variable number of strains that express all of the defined serogroup O2 subtype epitopes. Combination into one vaccine of two antigens that individually elicited cross-reactive opsonic antibodies to most members of the O2 serogroup inhibited, instead of enhanced, the production of antibodies broadly reactive with most serogroup O2 subtype strains. Thus, immune responses to P. aeruginosa O antigens may be restricted to a limited range of epitopes on structurally complex O antigens, and combining multiple related antigens into a single vaccine formulation may inhibit the production of those antibodies best able to protect against most P. aeruginosa strains within a given O-antigen serogroup.

  Lipopolysaccharide, Pseudomonas, Pseudomonas aeruginosa, O-polysaccharide, serology, serogroup, immune response

  NCBI PubMed ID: 9673254
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: gpier@channing.harvard.edu
  Institutions: Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115-5804., Charming Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School,Boston, Massachusetts 02115-5804.
  
   
  
  Pseudomonas aeruginosa Fisher 7
  CSDB ID 7219 (all data & tools)
• Article ID: 337
  Newton GJ, Daniels C, Burrows LL, Kropinski AM, Clarke AJ, Lam JS "Three-component-mediated serotype conversion in Pseudomonas aeruginosa by bacteriophage D3" - Molecular Microbiology 39(5) (2001) 1237-1247
  

  Bacteriophage D3 is capable of lysogenizing Pseudomonas aeruginosa PAO1 (serotype O5), converting the O-antigen from O5 to O16 and O-acetylating the N-acetylfucosamine moiety. To investigate the mechanism of lysogenic conversion, a 3.6 kb fragment from the D3 genome was isolated capable of mediating serotypic conversion identical to the D3 lysogen strain (AK1380). The PAO1 transformants containing this 3.6 kb of D3 DNA exhibited identical lipopolysaccharide (LPS) banding patterns to serotype O16 in silver-stained SDS-PAGE gels and displayed reactivity to an antibody specific for O-acetyl groups. Further analysis led to the identification of three open reading frames (ORFs) required for serotype conversion: an α-polymerase inhibitor (iap); an O-acetylase (oac); and a β-polymerase (wzyβ). The α-polymerase inhibitor (Iap) is capable of inhibiting the assembly of the serotype-specific O5 B-band LPS and allows the phage-encoded β-polymerase (Wzyβ) to form new β-linked B-band LPS. The D3 phage also alters the LPS by the addition of O-acetyl groups to the FucNAc residue in the O-antigen repeat unit by the action of the D3 O-acetylase (Oac). These three components form a simple yet elegant system by which bacteriophage D3 is capable of altering the surface of P. aeruginosa PAO1

  serotype, Pseudomonas, Pseudomonas aeruginosa, bacteriophage, conversion, serotype conversion

  NCBI PubMed ID: 11251840
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Microbiology, University of Guelph, Guelph, Ontario, N1G 2W1, Canada, The Centre for Infection and Biomaterials Research, Toronto General Hospital, Toronto, Ontario, M5G 2C4, Canada, Department of Microbiology and Immunology, Queen's University, Kingston, Ontario, K7L 3N6, Canada
  Methods: PCR, SDS-PAGE, DNA techniques, Western blotting, quantification of O-acetylation
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 7836 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa 7 Fisher
  CSDB ID 108490 (all data & tools)
• Article ID: 1832
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Kochetkov NK "Identification of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid in Pseudomonas aeruginosa immunotype 7 lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 992-994
  

  O-Specific polysaccharide chain of Pseudomonas aeruginosa immunotype 7 lipopolysaccharide is composed of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid (GulNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (ManN2Ac2A), and N-acetyl-D-fucosamine (FucNAc). On solvolysis with anhydrous hydrogen fluoride, the polysaccharide afforded a trisaccharide containing all its components. Borohydride reduction of the trisaccharide in boric acid solution resulted in conversion of reducing fucosamine into fucosaminitol, whereas in water the reduction was accompanied by reductive deamination of acetamidino function into ethylamino group. On hydrolysis with aqueous triethylamine, acetamidino group gave acetamido group. Analysis of the trisaccharides thus obtained by 1H NMR spectroscopy (including nuclear Overhauser effect), 13C NMR spectroscopy, and fast-atom bombardment mass spectrometry allowed the determination of the structure of the unusual uronic acid derivative and the following structure of the polysaccharide repeating unit: -4)-α-L-GulNAcAmA-(1-4)-β-D-ManN2Ac2A-(1-3)-α-D-FucNAc-(1-.

  NCBI PubMed ID: 2429670
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR
  
   
  
  Pseudomonas aeruginosa 7 Fisher
  CSDB ID 110531 (all data & tools)
• Article ID: 1842
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES "Antigenic polysaccharides of bacteria. 20. Structure of the O-specific polysaccharide chain of P. aeruginosa O3(a),3d,3f (Lányi) lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1649-1657
  

  Mild acid degradation of lipopolysaccharide from Pseudomonas aeruginosa O(3a), 3d, 3f (Lányi classification) afforded O-specific polysaccharide containing N-acetyl-D-fucosamine, 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid, 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic and D-mannuronic acid as well as O-acetyl groups. On the basis of O-deacetylation, selective cleavage with anhydrous fluoride, chemical transformation of the oligosaccharides obtained (hydrolysis or reductive deamination of the acetamidino group into acetamido or ethylamino group, respectively) and analysis by 13C NMR spectroscopy, it was concluded that the polysaccharide is built up mainly by trisaccharide repeating units of types A and B in the ratio approximately 2:1: (Formula: see text). The units of both types most probably enter the same polymeric chain. If so, such a hybrid structure can be accounted for by incompleteness of epimerization at C5 of the acetamidino derivative of mannuronic acid at the polymer level in the course of biosynthesis of this polysaccharide.

  NCBI PubMed ID: 2434103
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR
  
   
  
  Pseudomonas aeruginosa O(3a),3d,3f
  CSDB ID 110568 (all data & tools)
• Article ID: 1843
  Elkin YN, Knirel YA, Vinogradov EV, Paramonov NA, Troshkov ML, Aminev "Fast-atom-bombardment mass-spectra of aminooligosaccharides" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1658-1661
  
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: FAB-MS
  
   
  
  Pseudomonas aeruginosa
  CSDB ID 110580 (all data & tools)
• Article ID: 1844
  Knirel YA, Kocharova NA, Vinogradov EV, Paramonov NA, Dmitriev BA, Kochetkov NK, Stanislavsky ES, Kholodkova EV "Antigenic polysaccharides of bacteria. 21. Structure of O-specific polysaccharide chains and serological specificity of lipopolysaccharides of seven Pseudomonas aeruginosa immunotypes" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 13 (1987) 88-96
  

  On mild acid degradation on lipopolysaccharides of seven Pseudomonas aeruginosa immunotypes, O-specific polysaccharides were obtained and their structures established. A peculiar feature of the polysaccharides is the presence of various, mostly acidic, mono- and diaminosugars, many of which have not previously been found in nature. The absence of serological cross-reactions (inhibition of passive haemagglutination) between lipopolysaccharides of seven immunotypes correlates with the absence of any common oligosaccharide fragments in their O-specific chains. The data obtained revealed structural and serological interrelations between O-antigens of seven immunotypes and P. aeruginosa O-serotypes, and showed that immunotypes 1 and 7 should be included into the serological classification scheme as individual O-serotypes.

  NCBI PubMed ID: 2436629
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  
   
  
  Pseudomonas aeruginosa 7, Pseudomonas aeruginosa O2
  CSDB ID 110591 (all data & tools)
• Article ID: 2409
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Kholodkova EV, Stanislavsky ES "Somatic antigens of Pseudomonas aeruginosa. The structure of O-specific polysaccharide chains of lipopolysaccharides of P. aeruginosa O3 (Lányi), O25 (Wokatsch) and Fisher immunotypes 3 and 7" - European Journal of Biochemistry 167 (1987) 549-561
  

  O-specific polysaccharides, obtained on mild acid degradation of lipopolysacchrides of the serologically related strains Pseudomonas aeruginosa O3 (Lányi classification), O25 (Wokatsch classification) and immunotypes 3 and 7 (Fisher classification), are built up of trisaccharide repeating units involving 2-acetamido-2,6-dideoxy-D-galactose (N-acetyl-D-fucosamine), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid or 2,3-diacetamido-2,3-dideoxy-L-guluronic acid and 3-acetamidino-2-acetamido-2,3-dideoxy-D-mannuronic acid or 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid. Lányi O3(a),3d,3f and Wokatsch O25 polysaccharides contain also O-acetyl groups. On the basis of solvolysis with anhydrous hydrogen fluoride, resulting in trisaccharide fragments with N-acetylfucosamine residue at the reducing terminus, chemical modifications of the acetamidino group (alkaline hydrolysis to the acetamido group or reductive deamination to the ethylamino group), as well as analysis by 1H-NMR (including nuclear Overhauser effect experiments) and 13C-NMR spectroscopy, and fast-atom bombardment mass spectrometry, it was concluded that the repeating units of the polysaccharides have the following structures: (Formula: see text) where HexNAcAmA = α-L-GulNAcAmA (approximately 70%) or β-D-ManNacAMA (approximately 30%). Lányi O3(a),3d,3f polysaccharide involves two types of repeating units, which differ from each other only in the configuration at C-5 of the 3-acetamidino-2-acetamido-2,3-dideoxyuronic acid residue. Lányi O3(a),3c,O3a,3d,3e and Fisher immunotypes 3 and 7 polysaccharides contain, together with the major repeating units shown above, a small proportion of units in which the derivative of α-L-guluronic acid is replaced by the corresponding β-D-manno isomer. The data obtained provide the opportunity to substantiate the serological interrelations between these strains of P. aeruginosa by the presence in the O-specific polysaccharides of common monosaccharides or disaccharide fragments. The distinctions between them stem from the presence or absence of the O-acetyl group, a different configuration of the glycosidic linkage of the N-acetylfucosamine residue and/or a different configuration at C-5 of one or both derivatives of diaminouronic acids.

  NCBI PubMed ID: 3115777
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR, FAB-MS
  
   
  
  Pseudomonas aeruginosa Fisher 7
  CSDB ID 123053 (all data & tools)
• Article ID: 3207
  Knirel YA, Bystrova OV, Kocharova NA, Zähringer U, Pier GB "Conserved and variable structural features of the Pseudomonas aeruginosa lipopolysaccharide" - Journal of Endotoxin Research 12(6) (2006) 324-336
  

  The review is devoted to recent progress in the structural elucidation of the lipopolysaccharide of the bacterium Pseudomonas aeruginosa, including O-antigen biological repeats, core oligosaccharide, and lipid A. Data on biosynthesis, genetics and serology of the lipopolysaccharide isolated from various P. aeruginosa O-serogroups are discussed in relation to the chemical structures.

  O-antigen, Pseudomonas aeruginosa, lipid A, core oligosaccharide, lipopolysaccharide structure, serologic activity

  NCBI PubMed ID: 17254386
  Publication DOI: 10.1179/096805106X118906
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Brigham and Women’s Hospital, Harvard Medical School, Boston, Massachusetts, USA
  Methods: NMR, chemical methods, MS, serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O18, Pseudomonas aeruginosa F7
  CSDB ID 20560 (all data & tools)
• Article ID: 3391
  Kaluzny K, Abeyrathne PD, Lam JS "Coexistence of Two Distinct Versions of O-Antigen Polymerase, Wzy-Alpha and Wzy-Beta, in Pseudomonas aeruginosa Serogroup O2 and Their Contributions to Cell Surface Diversity" - Journal of Bacteriology 189(11) (2007) 4141-4152
  

  Assembly of B-band LPS in Pseudomonas aeruginosa follows a Wzy-dependent pathway, requiring the O-antigen polymerase Wzy, and other proteins. The peptide sequences of the wzyα product from strains of serotypes O2, O5, and O16 are identical; but the O-units in O5 are α-glycosidic-linked, while those in O2 and O16 are β-linked. We hypothesized that a derivative of the D3 bacteriophage wzyβ is present in the chromosomes of O2 and O16, and that this gene is responsible for the β-linkage. By a combination of PCR and primer walking, wzyβ of both serotypes have been amplified and cloned. Both are identical, but only share 87.42% sequence identity with their xenolog in D3. A chromosomal knockout mutant of O16 wzyβ was made and it produces rough LPS devoid of B-band O antigen. The cloned wzyβ is capable of complementing the O16 wzyβ mutant, as well as cross-complementing a wzyα knockout mutant. However, in the latter case, the restored O-antigen was β-linked. Using RT-PCR, we showed that wzyα was transcribed in O2 and O16 strains and was functional since both of these genes could complement the wzyα mutant of O5. With the co-existence of wzyα and wzyβ in O2 and O16 and the B-band O polysaccharides in these being β-linked, we hypothesized that iap, an inhibitor of alpha-polymerase gene, must be present in these serotypes. Indeed, through PCR, TOPO cloning and nucleotide sequencing results, we verified the presence of iap in both O2 and O16 serotypes

  serotype, Pseudomonas aeruginosa, O-polysaccharide, serogroup, sequencing, O-antigen polymerase, rough LPS

  NCBI PubMed ID: 17384183
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: jlam@uoguelph.ca
  Institutions: University of Guelph, Department of Molecular and Cellular Biology, Guelph, Ontario, Canada N1G 2W1
  Methods: serological methods, genetic methods
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 21926 (all data & tools)
• Article ID: 4062
  Lam JS, Taylor VL, Islam ST, Hao Y, Kocincova D "Genetic and Functional Diversity of Pseudomonas aeruginosa Lipopolysaccharide" - Frontiers in Microbiology 2 (2011) 118
  

  Lipopolysccharide (LPS) is an integral component of the Pseudomonas aeruginosa cell envelope, occupying the outer leaflet of the outer membrane in this Gram-negative opportunistic pathogen. It is important for bacterium-host interactions and has been shown to be a major virulence factor for this organism. Structurally, P. aeruginosa LPS is composed of three domains, namely, lipid A, core oligosaccharide, and the distal O antigen (O-Ag). Most P. aeruginosa strains produce two distinct forms of O-Ag, one a homopolymer of D-rhamnose that is a common polysaccharide antigen (CPA, formerly termed A band), and the other a heteropolymer of three to five distinct (and often unique dideoxy) sugars in its repeat units, known as O-specific antigen (OSA, formerly termed B band). Compositional differences in the O units among the OSA from different strains form the basis of the International Antigenic Typing Scheme for classification via serotyping of different strains of P. aeruginosa. The focus of this review is to provide state-of-the-art knowledge on the genetic and resultant functional diversity of LPS produced by P. aeruginosa. The underlying factors contributing to this diversity will be thoroughly discussed and presented in the context of its contributions to host-pathogen interactions and the control/prevention of infection.

  Lipopolysaccharide, biosynthesis, virulence, serotyping, bacteriophage, motility, seroconversion, nucleotide sugars

  NCBI PubMed ID: 21687428
  Publication DOI: 10.3389/fmicb.2011.00118
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 26863 (all data & tools)
• Article ID: 4684
  Islam ST, Lam JS "Synthesis of bacterial polysaccharides via the Wzx/Wzy-dependent pathway" - Canadian Journal of Microbiology 60(11) (2014) 697-716
  

  The surfaces of bacteria mediate a multitude of functions in the environment and in an infected host, including adhesion to both biotic and abiotic substrata, motility, immune system interaction and (or) activation, biofilm formation, and cell-cell communication, with many of these features directly influenced by cell-surface glycans. In both Gram-negative and Gram-positive bacteria, the majority of cell-surface polysaccharides are produced via the Wzx/Wzy-dependent assembly pathway; these glycans include heteropolymeric O-antigen, enterobacterial common antigen, exopolysaccharide, spore coat, and capsule in diverse bacteria. The key components of this assembly pathway are the integral inner membrane Wzx flippase, Wzy polymerase, and Wzz chain-length regulator proteins, which until recently have resisted detailed structural and functional characterization. In this review, we have provided a comprehensive synthesis of the latest structural and mechanistic data for each protein, as well as an examination of substrate specificity for each assembly step and complex formation between the constituent proteins. To complement the unprecedented explosion of genomic-sequencing data for bacteria, we have also highlighted both classical and state-of-the-art methods by which encoded Wzx, Wzy, and Wzz proteins can be reliably identified and annotated, using the model Gram-negative bacterium Pseudomonas aeruginosa as an example data set. Lastly, we outline future avenues of research, with the aim of stimulating researchers to take the next steps in investigating the function of, and interplay between, the constituents of this widespread assembly scheme.

  Membrane Proteins, lipopolysaccharide (LPS), Wzx flippase, Wzy polymerase, Wzz polysaccharide copolymerase

  NCBI PubMed ID: 25358682
  Publication DOI: 10.1139/cjm-2014-0595
  Journal NLM ID: 0372707
  Publisher: National Research Council of Canada
  Correspondence: sislam@imm.cnrs.fr; jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON N1G 2W1, Canada
  Methods: SDS-PAGE, genetic methods, cloning
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 30279 (all data & tools)
• Article ID: 4932
  Taylor VL, Hoage JF, Thrane SW, Huszczynski SM, Jelsbak L, Lam JS "A Bacteriophage-Acquired O-Antigen Polymerase (Wzyb) from P. aeruginosa Serotype O16 Performs a Varied Mechanism Compared to Its Cognate Wzya" - Frontiers in Microbiology 7 (2016) 393
  

  Pseudomonas aeruginosa is a Gram-negative bacterium that produces highly varied lipopolysaccharide (LPS) structures. The O antigen (O-Ag) in the LPS is synthesized through the Wzx/Wzy-dependent pathway where lipid-linked O-Ag repeats are polymerized by Wzy. Horizontal-gene transfer has been associated with O-Ag diversity. The O-Ag present on the surface of serotypes O5 and O16, differ in the intra-molecular bonds, alpha and beta, respectively; the latter arose from the action of three genes in a serotype converting unit acquired from bacteriophage D3, including a beta-polymerase (Wzyβ). To further our understanding of O-polymerases, the inner membrane (IM) topology of Wzyβ was determined using a dual phoA-lacZα reporter system wherein random 3' gene truncations were localized to specific loci with respect to the IM by normalized reporter activities as determined through the ratio of alkaline phosphatase activity to β-galactosidase activity. The topology of Wzyβ developed through this approach was shown to contain two predominant periplasmic loops, PL3 (containing an RX10G motif) and PL4 (having an O-Ag ligase superfamily motif), associated with inverting glycosyltransferase reaction. Through site-directed mutagenesis and complementation assays, residues Arg(254), Arg(270), Arg(272), and His(300) were found to be essential for Wzyβ function. Additionally, like-charge substitutions, R254K and R270K, could not complement the wzyβ knockout, highlighting the essential guanidium side group of Arg residues. The O-Ag ligase domain is conserved among heterologous Wzy proteins that produce β-linked O-Ag repeat units. Taking advantage of the recently obtained whole-genome sequence of serotype O16 a candidate promoter was identified. Wzyβ under its native promoter was integrated in the PAO1 genome, which resulted in simultaneous production of α- and β-linked O-Ag. These observations established that members of Wzy-like family consistently exhibit a dual-periplasmic loops topology, and identifies motifs that are plausible to be involved in enzymatic activities. Based on these results, the phage-derived Wzyβ utilizes a different reaction mechanism in the P. aeruginosa host to avoid self-inhibition during serotype conversion.

  Lipopolysaccharide, serotype, Pseudomonas aeruginosa, glycosyltransferase, bacteriophage, O-antigen biosynthesis, polymerase

  NCBI PubMed ID: 27065964
  Publication DOI: 10.3389/fmicb.2016.00393
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: jlam@uoguelph.ca
  Institutions: Department of Molecular and Cellular Biology, University of Guelph Guelph, ON, Canada, Department of Systems Biology, Technical University of Denmark Kongens Lyngby, Denmark
  Methods: PCR, SDS-PAGE, Western blotting, genetic methods, enzymatic assay
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 11743 (all data & tools)
• 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: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: 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
  
   
  
  Pseudomonas aeruginosa O18
  CSDB ID 9106 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: O-unit
Compound class: O-polysaccharide, O-antigen

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 2836 (all data & tools)
• Article ID: 1452
  Chatterjee SN, Chaudhuri K "Lipopolysaccharides of Vibrio cholerae. I. Physical and chemical characterization" - Biochimica et Biophysica Acta 1639(2) (2003) 65-79
  

  Vibrio cholerae is the causative organism of the disease cholera. The lipopolysaccharide (LPS) of V. cholerae plays an important role in eliciting the antibacterial immune response of the host and in classifying the vibrios into some 200 or more serogroups. This review presents an account of our up-to-date knowledge of the physical and chemical characteristics of the three constituents, lipid-A, core-polysaccharide (core-PS) and O-antigen polysaccharide (O-PS), of the LPS of V. cholerae of different serogroups including the disease-causing ones, O1 and O139. The structure and occurrence of the capsular polysaccharide (CPS) on V. cholerae O139 have been discussed as a relevant topic. Similarity and dissimilarity between the structures of LPS of different serogroups, and particularly between O22 and O139, have been analysed with a view to learning their role in the causation of the epidemic form of the disease by avoiding the host defence mechanism and in the evolution of the newer pathogenic strains in future. An idea of the emerging trends of research involving the use of immunogens prepared from synthetic oligosaccharides that mimic terminal epitopes of the O-PS of V. cholerae O1 in the development of a conjugate anti cholera vaccine is also discussed.

  Lipopolysaccharide, structure, lipid A, capsular polysaccharide, serogroup, Vibrio cholerae

  NCBI PubMed ID: 14559113
  Publication DOI: 10.1016/j.bbadis.2003.08.004
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Correspondence: sncac@sify.com (S.N. Chatterjee)
  Institutions: Saha Institute of Nuclear Physics, 1/AF Bidhannagar, Sector-1, Calcutta-700 064, India, Biophysics Division, Indian Institute of Chemical Biology, Jadavpur, Calcutta-700 032, India
  
   
  
  Vibrio cholerae O8
  CSDB ID 31698 (all data & tools)
• Article ID: 1469
  Knirel YA, Perepelov AV "Trifluoromethanesulfonic acid: a useful reagent for the solvolytic cleavage of glycosidic linkages in structural analysis of bacterial polysaccharides" - Australian Journal of Chemistry 55(1-2) (2002) 69-72
  

  The initial data on the application of triflic acid was summarized for the isolation of complex monosachharide derivatives and oligosachharides in the structural analysis of various bacterial polysachharides. Solvolysis proceeded selectively and without destruction of the sugars. Varying the temperature and duration of the reaction enabled preparation of oligosaccharides of different sizes.

  polysaccharide, structural analysis, bacterial polysaccharides, solvolysis, trifluoromethanesulfonic acid, triflic acid

  Publication DOI: 10.1071/CH01181
  Journal NLM ID: 0370614
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, GLC, MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 31914 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Vibrio cholerae O8
  CSDB ID 27772 (all data & tools)
• Article ID: 5157
  Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Streptococcus suis serotype 3 and serotype 18 capsular polysaccharides contain di-N-acetyl-bacillosamine" - Carbohydrate Research 466 (2018) 18-29
  

  Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n. To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report. This led to the identification of homologues of UDP-QuiNAc4NAc synthesis genes in S. suis serotype 18. Thus, the repeating unit sequence for serotype 18 is: [3)d-GalNAc(α1-3)[d-Glc (β1-2)]d-GalA4OAc(β1-3)d-GalNAc(α1-3)d-QuiNAc4NAc(α1-]n. A correlation between S. suis serotypes 3 and 18 CPS sequences and genes of these serotypes' cps loci encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotypes 3 and 18.

  polysaccharide, capsular polysaccharide, polysaccharides, carbohydrate structure, Streptococcus suis, Di-N-Acetyl-bacillosamine, Serotype 18, Serotype 3

  NCBI PubMed ID: 30014879
  Publication DOI: 10.1016/j.carres.2018.07.003
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: mariela.segura@umontreal.ca
  Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
  Methods: 13C NMR, 1H NMR, periodate oxidation, gel filtration, NMR-2D, GC-MS, de-O-acylation, sugar analysis, methanolysis, SEC-MALS, bioinformatic analysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 12603 (all data & tools)
• 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: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: 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
  
   
  
  Vibrio cholerae O8
  CSDB ID 9119 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 3033 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 3034 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 3035 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 3036 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 872
  Kocharova NA, Perepelov AV, Zatonsky GV, Shashkov AS, Knirel YA, Jansson P, Weintraub A "Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid" - Carbohydrate Research 330(1) (2001) 83-92
  

  The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: →4)-β-D-Glcp NAc3NAcylAN-(1→4)-β-D-Manp NAc3NAcAN-(1→4)-α-L-Gulp NAc3NAcA-(1→3)-β-D-QuipNAc4NAc-(1→ where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of β-QuiNAc4NAc and α-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.

  Lipopolysaccharide, O-specific polysaccharide, O-Specific polysaccharide structure, 2, 3-diamino-2, Vibrio cholerae, 3-dideoxyhexuronic acid, triflic acid solvolysis, solvolysis

  NCBI PubMed ID: 11217966
  Publication DOI: 10.1016/S0008-6215(00)00271-8
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pererik.jansson@kfcmail.hs.sii.se
  Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
  Methods: NMR, HF solvolysis, ESI-MS, triflic acid solvolysis
  
   
  
  Vibrio cholerae O8
  CSDB ID 3037 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit

• Article ID: 1412
  de Kievit TR, Staples T, Lam JS "Pseudomonas aeruginosa rfc genes of serotypes O2 and O5 could complement O-polymerase-deficient semi-rough mutants of either serotype" - FEMS Microbiology Reviews 147(2) (1997) 251-257
  

  Using a gene-replacement strategy and a mutated copy of the Pseudomonas aeruginosa O5 rfc gene, we were able to generate a rfc mutant in P. aeruginosa serotype O2. This mutant, which exhibits the semi-rough (SR) LPS phenotype, was used to isolate the O2 rfc gene. Mobilization of the O2 and O5 rfc genes into SR mutants of the heterologous serotype resulted in 'cross-polymerization' of O-repeat units, indicating that the genes are functionally exchangeable. Analysis of the nucleotide sequence of the rfc genes revealed that the two Rfc proteins are identical. The results of this study have enabled us to propose the linkage catalyzed by the O5 O-polymerase enzyme.

  Lipopolysaccharide, LPS, gene, serotype, Pseudomonas, Pseudomonas aeruginosa, mutant, mutants, Serotypes, O-antigen polymerase, rfc, complement, semirough

  NCBI PubMed ID: 9119201
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: jlam@micro.uoguelph.ca
  Institutions: Department of Microbiology, University of Guelph, Guelph, Canada
  
   
  
  Pseudomonas aeruginosa O16, Pseudomonas aeruginosa O20
  CSDB ID 6655 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide

• Article ID: 1627
  Kilcoyne M, Shashkov AS, Knirel YA, Gorshkova RP, Nazarenko EL, Ivanova EP, Gorshkova NM, Senchenkova SN, Savage AV "The structure of the O-polysaccharide of the Pseudoalteromonas rubra ATCC 29570T lipopolysaccharide containing a keto sugar" - Carbohydrate Research 340(15) (2005) 2369-2375
  

  The structure of the phenol-soluble polysaccharide from Pseudoalteromonas rubra type strain ATCC 29570T has been elucidated using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, gNOESY, ROESY, 1H,13C gHMQC and gHMBC experiments. It is concluded that the trisaccharide repeating unit of the polysaccharide has the following structure: [carbohydrate structure: see text] where Sug is 2-acetamido-2,6-dideoxy-D-xylo-hexos-4-ulose, Am is acetimidoyl and Acyl is a malic acid residue, which is O-acetylated in approximately 70% of the units.

  Lipopolysaccharide, structure, strain, polysaccharide, type, O-polysaccharide, O polysaccharide, O-specific, O-specific polysaccharide, sugar, sugars, Shewanella, amino, keto sugar, amino sugar, Pseudoalteromonas, amino sugars

  NCBI PubMed ID: 16126182
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: angela.savage@nuigalway.ie
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Science, Vladivostok 690022, Russian Federation
  Methods: NMR, composition analysis
  
   
  
  Vibrio ordalii O2
  CSDB ID 10728 (all data & tools)
• Article ID: 4554
  Kokoulin MS, Kalinovsky AI, Komandrova NA, Tovarchi VE, Tomshich SV, Nedashkovskaya OI, Vaskovsky VE "The structure of the O-specific polysaccharide from marine bacterium Litorimonas taeanensis G5 containing 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-D-quinovose and 2-acetamido-2,6-dideoxy-L-xylo-hexos-4-ulose" - Carbohydrate Research 375 (2013) 105-111
  

  The O-polysaccharide was isolated from the lipopolysaccharide of Litorimonas taeanensis G5T and studied by chemical methods along with 1H and 13C NMR spectroscopy, including 1H, 1H COSY, 1D and 2D TOCSY, NOESY, 1H, 13C HSQC, HMBC, and H2BC experiments. The following new structure of the O-polysaccharide of L. taeanensis G5T containing 2-acetamido-2-deoxy-d-galacturonic acid (d-GalNAcA), 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-d-quinovose (d-QuiNAc4NR), and 2-acetamido-2,6-dideoxy-l-xylo-hexos-4-ulose (l-Sug) was established: where R is (3S,5S)-3,5-dihydroxyhexanoic acid.

  O-specific polysaccharide, 2-acetamido-2, 6-dideoxy-L-xylo-hexos-4-ulose, 2-Acetamido-4-((3S, 5S)-3, 5-dihydroxyhexanamido)-2, 4-dideoxy-D-quinovose, Litorimonas taeanensis

  NCBI PubMed ID: 23694711
  Publication DOI: 10.1016/j.carres.2013.04.004
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, NMR-1D, triflic acid solvolysis, borohydride reduction
  
   
  
  Vibrio ordalii O2
  CSDB ID 29614 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide

• Article ID: 1627
  Kilcoyne M, Shashkov AS, Knirel YA, Gorshkova RP, Nazarenko EL, Ivanova EP, Gorshkova NM, Senchenkova SN, Savage AV "The structure of the O-polysaccharide of the Pseudoalteromonas rubra ATCC 29570T lipopolysaccharide containing a keto sugar" - Carbohydrate Research 340(15) (2005) 2369-2375
  

  The structure of the phenol-soluble polysaccharide from Pseudoalteromonas rubra type strain ATCC 29570T has been elucidated using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, gNOESY, ROESY, 1H,13C gHMQC and gHMBC experiments. It is concluded that the trisaccharide repeating unit of the polysaccharide has the following structure: [carbohydrate structure: see text] where Sug is 2-acetamido-2,6-dideoxy-D-xylo-hexos-4-ulose, Am is acetimidoyl and Acyl is a malic acid residue, which is O-acetylated in approximately 70% of the units.

  Lipopolysaccharide, structure, strain, polysaccharide, type, O-polysaccharide, O polysaccharide, O-specific, O-specific polysaccharide, sugar, sugars, Shewanella, amino, keto sugar, amino sugar, Pseudoalteromonas, amino sugars

  NCBI PubMed ID: 16126182
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: angela.savage@nuigalway.ie
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Chemistry, National University of Ireland, Galway, Ireland, Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Science, Vladivostok 690022, Russian Federation
  Methods: NMR, composition analysis
  
   
  
  Vibrio anguillarum O2
  CSDB ID 10729 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Listonella anguillarum O2a
  CSDB ID 27796 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen

• Article ID: 1832
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Kochetkov NK "Identification of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid in Pseudomonas aeruginosa immunotype 7 lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 992-994
  

  O-Specific polysaccharide chain of Pseudomonas aeruginosa immunotype 7 lipopolysaccharide is composed of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid (GulNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (ManN2Ac2A), and N-acetyl-D-fucosamine (FucNAc). On solvolysis with anhydrous hydrogen fluoride, the polysaccharide afforded a trisaccharide containing all its components. Borohydride reduction of the trisaccharide in boric acid solution resulted in conversion of reducing fucosamine into fucosaminitol, whereas in water the reduction was accompanied by reductive deamination of acetamidino function into ethylamino group. On hydrolysis with aqueous triethylamine, acetamidino group gave acetamido group. Analysis of the trisaccharides thus obtained by 1H NMR spectroscopy (including nuclear Overhauser effect), 13C NMR spectroscopy, and fast-atom bombardment mass spectrometry allowed the determination of the structure of the unusual uronic acid derivative and the following structure of the polysaccharide repeating unit: -4)-α-L-GulNAcAmA-(1-4)-β-D-ManN2Ac2A-(1-3)-α-D-FucNAc-(1-.

  NCBI PubMed ID: 2429670
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR
  
   
  
  Pseudomonas aeruginosa 7 Fisher
  CSDB ID 110532 (all data & tools)
• Article ID: 1842
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES "Antigenic polysaccharides of bacteria. 20. Structure of the O-specific polysaccharide chain of P. aeruginosa O3(a),3d,3f (Lányi) lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1649-1657
  

  Mild acid degradation of lipopolysaccharide from Pseudomonas aeruginosa O(3a), 3d, 3f (Lányi classification) afforded O-specific polysaccharide containing N-acetyl-D-fucosamine, 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid, 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic and D-mannuronic acid as well as O-acetyl groups. On the basis of O-deacetylation, selective cleavage with anhydrous fluoride, chemical transformation of the oligosaccharides obtained (hydrolysis or reductive deamination of the acetamidino group into acetamido or ethylamino group, respectively) and analysis by 13C NMR spectroscopy, it was concluded that the polysaccharide is built up mainly by trisaccharide repeating units of types A and B in the ratio approximately 2:1: (Formula: see text). The units of both types most probably enter the same polymeric chain. If so, such a hybrid structure can be accounted for by incompleteness of epimerization at C5 of the acetamidino derivative of mannuronic acid at the polymer level in the course of biosynthesis of this polysaccharide.

  NCBI PubMed ID: 2434103
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR
  
   
  
  Pseudomonas aeruginosa O(3a),3d,3f
  CSDB ID 110570 (all data & tools)
• Article ID: 1843
  Elkin YN, Knirel YA, Vinogradov EV, Paramonov NA, Troshkov ML, Aminev "Fast-atom-bombardment mass-spectra of aminooligosaccharides" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1658-1661
  
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: FAB-MS
  
   
  
  Pseudomonas aeruginosa
  CSDB ID 110586 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen

• Article ID: 1832
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Kochetkov NK "Identification of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid in Pseudomonas aeruginosa immunotype 7 lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 992-994
  

  O-Specific polysaccharide chain of Pseudomonas aeruginosa immunotype 7 lipopolysaccharide is composed of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid (GulNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (ManN2Ac2A), and N-acetyl-D-fucosamine (FucNAc). On solvolysis with anhydrous hydrogen fluoride, the polysaccharide afforded a trisaccharide containing all its components. Borohydride reduction of the trisaccharide in boric acid solution resulted in conversion of reducing fucosamine into fucosaminitol, whereas in water the reduction was accompanied by reductive deamination of acetamidino function into ethylamino group. On hydrolysis with aqueous triethylamine, acetamidino group gave acetamido group. Analysis of the trisaccharides thus obtained by 1H NMR spectroscopy (including nuclear Overhauser effect), 13C NMR spectroscopy, and fast-atom bombardment mass spectrometry allowed the determination of the structure of the unusual uronic acid derivative and the following structure of the polysaccharide repeating unit: -4)-α-L-GulNAcAmA-(1-4)-β-D-ManN2Ac2A-(1-3)-α-D-FucNAc-(1-.

  NCBI PubMed ID: 2429670
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR
  
   
  
  Pseudomonas aeruginosa 7 Fisher
  CSDB ID 110533 (all data & tools)
• Article ID: 1842
  Knirel YA, Paramonov NA, Vinogradov EV, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES "Antigenic polysaccharides of bacteria. 20. Structure of the O-specific polysaccharide chain of P. aeruginosa O3(a),3d,3f (Lányi) lipopolysaccharide" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1649-1657
  

  Mild acid degradation of lipopolysaccharide from Pseudomonas aeruginosa O(3a), 3d, 3f (Lányi classification) afforded O-specific polysaccharide containing N-acetyl-D-fucosamine, 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid, 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic and D-mannuronic acid as well as O-acetyl groups. On the basis of O-deacetylation, selective cleavage with anhydrous fluoride, chemical transformation of the oligosaccharides obtained (hydrolysis or reductive deamination of the acetamidino group into acetamido or ethylamino group, respectively) and analysis by 13C NMR spectroscopy, it was concluded that the polysaccharide is built up mainly by trisaccharide repeating units of types A and B in the ratio approximately 2:1: (Formula: see text). The units of both types most probably enter the same polymeric chain. If so, such a hybrid structure can be accounted for by incompleteness of epimerization at C5 of the acetamidino derivative of mannuronic acid at the polymer level in the course of biosynthesis of this polysaccharide.

  NCBI PubMed ID: 2434103
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: 13C NMR, 1H NMR
  
   
  
  Pseudomonas aeruginosa O(3a),3d,3f
  CSDB ID 110574 (all data & tools)
• Article ID: 1843
  Elkin YN, Knirel YA, Vinogradov EV, Paramonov NA, Troshkov ML, Aminev "Fast-atom-bombardment mass-spectra of aminooligosaccharides" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1658-1661
  
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
  Methods: FAB-MS
  
   
  
  Pseudomonas aeruginosa
  CSDB ID 110585 (all data & tools)