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1. Compound ID: 27
Structure type: polymer chemical repeating unit
Trivial name: mannan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 10
Beynon LM, Cox AD, Taylor CJ, Wilkinson SG, Perry MB "Characterization of a lipopolysaccharide containing two different trisaccharide repeating units from Burkholderia cepacia serotype E (O2)" -
Carbohydrate Research 272 (1995) 231-239
The O antigen of the lipopolysaccharide of Burkholderia cepacia serotype E (O2) was shown by a combination of methylation analysis, partial hydrolysis, NMR, and mass spectrometric methods to be a high molecular weight polysaccharide composed of two different trisaccharide repeating units in the ratio 2:1. The major trisaccharide component is composed of two α-D-mannopyranosyl and one β-D-galactopyranosyl residues with the structure, [→2)-α-D-Manp-(1→2)-α-D-Manp-(1→4)-β-D-Galp-(1→]n The minor trisaccharide component is a D-mannan composed of two α- and one β-D-mannopyranosyl residues with the structure, [→2)-α-D-Manp-(1→2)-α-D-Manp-(1→3)-β-D-Manp-(1→]n
Lipopolysaccharide, LPS, structure, characterization, serotype, methylation analysis, 2D NMR (COSY, NOESY) experiments, GCL-MC of alditol acetates, FASBMS, Burkholderia, Burkholderia cepacia, D-mannose, O-antigen, repeating unit, trisaccharide
NCBI PubMed ID: 7497480Publication DOI: 10.1016/0008-6215(95)00095-bJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, FAB-MS, partial acid hydrolysis
- Article ID: 183
Vinogradov E, Frirdich E, MacLean LL, Perry MB, Petersen BO, Duus JO, Whitfield C "Structures of lipopolysaccharides from Klebsiella pneumoniae. Eluicidation of the structure of the linkage region between core and polysaccharide O chain and identification of the residues at the non- reducing termini of the O chains" -
Journal of Biological Chemistry 277(28) (2002) 25070-25081
Deamination of LPSs from Klebsiella pneumoniae released O-chain polysaccharides together with a fragment of the core oligosaccharide. The structures of the products from serotypes O1, O2a, O2a,c, O3, O4, O5, and O12 were determined by NMR spectroscopy and chemical methods, identifying the linkage region between the O antigens and the core as well as novel residues at the non-reducing ends of the polysaccharides. All serotypes had an identical linkage between the O chain and core.
lipopolysaccharides, oligosaccharide, structure, core oligosaccharide, NMR spectroscopy, O-antigens, linkage, region, O-chain, Klebsiella pneumoniae, reducing
NCBI PubMed ID: 11986326Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0R6, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Carlsberg Laboratory, Department of Chemistry, Gamle Carlsberg Vej 10, DK-2500 Valby, Copenhagen, Denmark
Methods: NMR-2D, NMR, serological methods, genetic methods
- Article ID: 405
Vinion-Dubiel AD, Goldberg JB "Lipopolysaccharide of Burkholderia cepacia complex" -
Journal of Endotoxin Research 9(4) (2003) 201-213
Burkholderia cepacia complex (Bcc) is a group of phenotypically similar, genetically distinct bacteria that are beneficial to the environment but can also cause severe human infections. Bcc are being exploited for use as bioremediation agents and as a way to combat agricultural plant diseases. However, Bcc can cause lung infections in patients with chronic granulomatous disease or cystic fibrosis often resulting in mortality of these patients. Since it is unclear what bacterial components are necessary for causing human infections, studies of Bcc have focused on identifying putative virulence factors. As in other Gram-negative bacteria, the lipopolysaccharide (LPS) of Bcc induces a strong immune response that can contribute to host cell damage. The unusual structure of Bcc LPS lowers the anionic charge of the Bcc cell surface, which inhibits the binding and subsequent effects of cationic antibiotics. These distinguishing features include the substitution of a Ko for a Kdo residue in the inner core oligosaccharide and Ara4N residues bound to phosphates of the lipid A backbone. The structures of O antigen subunits and the consequent serotypes will also be discussed, with particular reference to the O antigen biosynthetic loci of two Bcc strains.
Lipopolysaccharide, structure, Burkholderia, Burkholderia cepacia, O-antigen, complex, endotoxin, Re
NCBI PubMed ID: 12935351Publication DOI: 10.1177/09680519030090040101Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Microbiology, University of Virginia Health Sciences Center, Charlottesville, VA 22908-0734, USA
- Article ID: 619
Aucken HM, Wilkinson SG, Pitt TL "Immunochemical characterization of two new O serotypes of Serratia marcescens (O27 and O28)" -
FEMS Microbiology Letters 138 (1996) 77-82
In an earlier study of the distribution of O-serotypes among clinical isolates of Serratia marcescens, two apparently new serotypes were identified, represented by strains S1254 and S3255. Studies using ELISA, immunoblotting and the Quellung reaction have shown that they qualify for inclusion in the O-antigenic typing scheme on three counts: (1) they possess chemically distinct O-antigenic repeating units, (2) the O-antigens are serologically distinguishable from all others, and (3) they are found in a significant proportion of clinical S. marcescens strains (LWr and We respectively), S1254, the type strain for serotype 027, is an acapsular strain which expressed a glucorhamnan with a disaccharide repeating unit as its lipopolysaccharide side chain. It cross-reacts with serotype 04, the 0 antigen of which is an O-acetylated form of the 027 glucorhamnan, but this cross-reaction can be eliminated by reciprocal cross-absorption. S3255. the type strain for serotype 028, has a mannose homopolymer as its O-antigen and is the only S. marcescens serotype with a trimeric repeating-unit structure. However, it cross-reacts with the 05 serotype strain due to similarities in their acidic capsular polysaccharides. Cross-absorption and the production of serum to an acapsular variant of serotype strain 02S produced typing reagents which could differentiate serotypes 05 and 028.
Lipopolysaccharide, LPS, polysaccharide, serotype, Serratia marcescens, immunochemical, Serratia, serotyping, O-serotype
NCBI PubMed ID: 8674974Journal NLM ID: 7705721Publisher: Blackwell Publishing
Institutions: Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, Quellung reaction
- Article ID: 620
Aucken HM, Wilkinson SG, Pitt TL "Re-evaluation of the serotypes of Serratia marcescens and separation into two schemes based on lipopolysaccharide (O) and capsular polysaccharide (K) antigens" -
Microbiology 144 (1998) 639-653
Chemical and serological analysis has revealed that many of the 29 O serotype reference strains of Serratia marcescens contain both neutral and acidic polysaccharides which correspond to LPS O antigens and capsular K antigens, respectively. New O and K antigen typing schemes have therefore been devised, based on the known chemical structures of the surface polysaccharides of the organism. These schemes were designed to allow the specific detection of these antigens on unknown strains using ELISAs. O antigens were detected using whole cells cultured in broth then autoclaved to remove capsular material, while K antigens were detected using formolized whole cells which had been cultured on glycerol agar to enhance capsule production. After testing with the 29 reference strains as well as 423 distinct clinical strains, it was apparent that different aspects of chemical structure were associated with different degrees of serological reactivity and the typing schemes were modified further to accommodate this. In general, the O antigen repeating unit structures were chemically simple with di- or trisaccharide backbones. Serological specificity was often provided solely by the presence or absence of an O-acetyl substituent, or a change in the linkage between two sugar residues. Five of the O serotypes in the new scheme were represented by 12 of the 29 reference strains, while three reference strains lacked O antigens altogether, resulting in the elimination of 10 of the original O types. In contrast, the K antigen repeating unit structures were more complex and chemically diverse, having at least four sugar residues. Three K types were each seen in two reference strains while 12 of the 29 reference strains were acapsular. Thus, the resulting schemes contain 19 O types and 14 K types and allow the definitive serotype identification of S. marcescens.
Lipopolysaccharide, antigen, LPS, structure, K-antigen, O-antigen, capsular polysaccharide, Serratia marcescens, Serratia, serotyping, O-serotype
NCBI PubMed ID: 9534235Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: haucken@phls.co.uk
Institutions: Laboratory of Hospital Infection, Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University, Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, chromatography, Quellung reaction, serum adsorption assays
- Article ID: 745
Kido N, Torgov VI, Sugiyama T, Uchiya K, Sugihara H, Komatsu T, Kato N, Jann K "Expression of the O9 polysaccharide of Escherichia coli: sequencing of the E. coli O9 rfb gene cluster, characterization of mannosyl transferases, and evidence for an ATP-binding cassette transport system" -
Journal of Bacteriology 177(8) (1995) 2178-2187
The rfb gene cluster of Escherichia coli O9 directs the synthesis of the O9-specific polysaccharide which has the structure →2-α-Man-(1→2)-α-Man-(1→2)-α-Man-(1→3)-α-Man-(1→. The E. coli O9 rfb cluster has been sequenced, and six genes, in addition to the previously described rfbK and rfbM, were identified. They correspond to six open reading frames (ORFs) encoding polypeptides of 261, 431, 708, 815, 381, and 274 amino acids. They are all transcribed in the counter direction to those of the his operon. No gene was found between rfb and his. A higher G+C content indicated that E. coli O9 rfb evolved independently of the rfb clusters from other E. coli strains and from Shigella and Salmonella spp. Deletion mutagenesis, in combination with analysis of the in vitro synthesis of the O9 mannan in membranes isolated from the mutants, showed that three genes (termed mtfA, -B, and -C, encoding polypeptides of 815, 381, and 274 amino acids, respectively) directed α-mannosyl transferases. MtfC (from ORF274), the first mannosyl transferase, transfers a mannose to the endogenous acceptor. It critically depended on a functional rfe gene (which directs the synthesis of the endogenous acceptor) and initiates the growth of the polysaccharide chain. MtfB (from ORF381) then transfers two mannoses into the 3 position of the previous mannose, and MtfA (from ORF815) transfers three mannoses into the 2 position. Further chain growth needs only the two transferases MtfA and MtfB. Thus, there are fewer transferases needed than the number of sugars in the repeating unit. Analysis of the predicted amino acid sequence of the ORF261 and ORF431 proteins indicated that they function as components of an ATP-binding cassette transport system. A possible correlation between the mechanism of polymerization and mode of membrane translocation of the products is discussed.
biosynthesis, expression, gene, characterization, polysaccharide, O-antigen, Escherichia, Escherichia coli, rfb, transferase, cluster, gene cluster, sequencing, rfb gene cluster, Mannose, mannan, transport, transferases
NCBI PubMed ID: 7536735Publication DOI: 10.1128/jb.177.8.2178-2187.1995Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Max-Planck-Institute für Immunobiologie, Freiburg, Germany
Methods: DNA techniques
- Article ID: 1610
Cuthbertson L, Powers J, Whitfield C "The C-terminal domain of the nucleotide-binding domain protein Wzt determines substrate specificity in the ATP-binding cassette transporter for the lipopolysaccharide O-antigens in Escherichia coli serotypes O8 and O9a" -
Journal of Biological Chemistry 280(34) (2005) 30310-30319
The polymannan O-antigenic polysaccharides (O-PSs) of Escherichia coli O8 and O9a are synthesized via an ATP-binding cassette (ABC) transporter-dependent pathway. The group 2 capsular polysaccharides of E. coli serve as prototypes for polysaccharide synthesis and export via this pathway. Here, we show that there are some fundamental differences between the ABC transporter-dependent pathway for O-PS biosynthesis and the capsular polysaccharide paradigm. In the capsule system, mutants lacking the ABC transporter are viable, and membranes isolated from these strains are no longer able to synthesize polymer using an endogenous acceptor. In contrast, E. coli strains carrying mutations in the membrane component (Wzm) and/or the nucleotide-binding component (Wzt) of the O8 and O9a polymannan transporters are nonviable under conditions permissive to O-PS biosynthesis and take on an aberrant elongated cell morphology. Whereas the ABC transporters for capsular polysaccharides with different structures are functionally interchangeable, the O8 and O9a exporters are specific for their cognate polymannan substrates. The E. coli O8 and O9a Wzt proteins contain a C-terminal domain not present in the corresponding nucleotide-binding protein (KpsT) from the capsule exporter. Whereas the Wzm components are functionally interchangeable, albeit with reduced efficiency, the Wzt components are not, indicating a specific role for Wzt in substrate specificity. Chimeric Wzt proteins were constructed in order to localize the region involved in substrate specificity to the C-terminal domain
Escherichia coli, ABC transporter, ATP-Binding Cassette Transporters, Wzt
NCBI PubMed ID: 15980069Publication DOI: 10.1074/jbc.M504371200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: cwhitfie@uoguelph.ca
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada
Methods: genetic methods
- Article ID: 1674
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
- Article ID: 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 2187
Oxley D, Wilkinson SG "Structure of a mannan isolated from the lipopolysaccharide of the reference strain (S3255) for a new serogroup of Serratia marcescens" -
Carbohydrate Research 212 (1991) 213-217
Both a neutral and an acidic polymer have been isolated from a lipopolysaccharide extract of Serratia marcescens strain S3255. The neutral polymer is a linear mannan with the repeating unit shown. The same repeating unit has been described for the O-specific polymers from Escherichia coli O8 and Klebsiella O5.
NCBI PubMed ID: 1959117Publication DOI: 10.1016/0008-6215(91)84058-mJournal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, The University, Hull, Great Britain
- Article ID: 2484
Aucken HM, Pitt TL "Serological relationships of the O antigens of Klebsiella pneumoniae O5, Escherichia coli O8 and a new O serotype of Serratia marcescens" -
FEMS Microbiology Letters 80 (1991) 93-97
Journal NLM ID: 7705721Publisher: Blackwell Publishing
- Article ID: 3197
Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" -
FEMS Microbiology Reviews 30(3) (2006) 382-403
Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/
NMR, structure, serotype, O-antigen, Enterobacteriacea, database
NCBI PubMed ID: 16594963Publication DOI: 10.1111/j.1574-6976.2006.00016.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: andrej.weintraub@ki.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
- Article ID: 4103
Roslund MU, Sawen E, Landstrom J, Ronnols J, Jonsson KH, Lundborg M, Svensson MV, Widmalm G "Complete 1H and 13C NMR chemical shift assignments of mono-, di-, and trisaccharides as basis for NMR chemical shift predictions of polysaccharides using the computer program casper" -
Carbohydrate Research 346(11) (2011) 1311-1319
The computer program casper uses (1)H and (13)C NMR chemical shift data of mono- to trisaccharides for the prediction of chemical shifts of oligo- and polysaccharides. In order to improve the quality of these predictions the (1)H and (13)C, as well as (31)P when applicable, NMR chemical shifts of 30 mono-, di-, and trisaccharides were assigned. The reducing sugars gave two distinct sets of NMR resonances due to the α- and β-anomeric forms. In total 35 (1)H and (13)C NMR chemical shift data sets were obtained from the oligosaccharides. One- and two-dimensional NMR experiments were used for the chemical shift assignments and special techniques were employed in some cases such as 2D (1)H,(13)C-HSQC Hadamard Transform methodology which was acquired approximately 45 times faster than a regular t(1) incremented (1)H,(13)C-HSQC experiment and a 1D (1)H,(1)H-CSSF-TOCSY experiment which was able to distinguish spin-systems in which the target protons were only 3.3Hz apart. The (1)H NMR chemical shifts were subsequently refined using total line-shape analysis with the PERCH NMR software. The acquired NMR data were then utilized in the casper program (http://www.casper.organ.su.se/casper/) for NMR chemical shift predictions of the O-antigen polysaccharides from Klebsiella O5, Shigella flexneri serotype X, and Salmonella arizonae O62. The data were compared to experimental data of the polysaccharides from the two former strains and the lipopolysaccharide of the latter strain showing excellent agreement between predicted and experimental (1)H and (13)C NMR chemical shifts.
Lipopolysaccharide, chemical shift prediction, chemical shift filter, Hadamard matrix
NCBI PubMed ID: 21621752Publication DOI: 10.1016/j.carres.2011.04.033Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, NMR-1D, computer analysis with CASPER
- Article ID: 4305
Greenfield LK, Richards MR, Li J, Wakarchuk WW, Lowary TL, Whitfield C "Biosynthesis of the polymannose lipopolysaccharide O antigens from Escherichia coli serotypes O8 and O9a requires a unique combination of single- and multi-active site mannosyltransferases" -
Journal of Biological Chemistry 287(42) (2012) 35078-35091
The Escherichia coli O9a and O8 O-antigen serotypes represent model systems for the ABC transporter-dependent synthesis of bacterial polysaccharides. The O9a and O8 antigens are linear mannose homopolymers containing conserved reducing termini (the primer-adaptor), a serotype-specific repeat-unit domain, and a terminator. Synthesis of these glycans occurs on the polyisoprenoid lipid-linked primer, undecaprenyl pyrophosphoryl-GlcpNAc, by two conserved mannosyltransferases, WbdC and WbdB, and a serotype-specific mannosyltransferase, WbdA. The glycan structure and pattern of conservation in the O9a and O8 mannosyltransferases are not consistent with the existing model of O9a biosynthesis. Here we establish a revised pathway using a combination of in vivo (mutant complementation) experiments and in vitro strategies with purified enzymes and synthetic acceptors. WbdC and WbdB synthesize the adaptor region, where they transfer one and two α-(1→3)-linked mannose residues, respectively. The WbdA enzymes are solely responsible for forming the repeat-unit domains of these O antigens. WbdA(O9a) has two predicted active sites and polymerizes a tetrasaccharide repeat unit containing two α-(1→3)- and two α-(1→2)-linked mannopyranose residues. In contrast, WbdA(O8) polymerizes trisaccharide repeat units containing single α-(1→3), α-(1→2) and β-(1→2)-mannopyranoses. These studies illustrate assembly systems exploiting several mannosyltransferases with flexible active sites, arranged in single and multi-domain formats
biosynthesis, Escherichia coli, O-antigens, mannosyltransferases
NCBI PubMed ID: 22875852Publication DOI: 10.1074/jbc.M112.401000DAJournal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: cwhitfie@uoguelph.ca
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, DNA techniques, MALDI-TOF MS, NMR-1D, biochemical methods, computer analysis with CASPER, CE
- Article ID: 4306
Greenfield LK, Richards MR, Vinogradov E, Wakarchuk WW, Lowary TL, Whitfield C "Domain Organization of the Polymerizing Mannosyltransferases Involved in Synthesis of the Escherichia coli O8 and O9a Lipopolysaccharide O-antigens" -
Journal of Biological Chemistry 287(45) (2012) 38135-38149
The Escherichia coli O9a and O8 polymannose O-polysaccharides (O-PSs) serve as model systems for the biosynthesis of bacterial polysaccharides by ATP-binding cassette transporter-dependent pathways. Both O-PSs contain a conserved primer-adaptor domain at the reducing terminus and a serotype-specific repeat unit domain. The repeat unit domain is polymerized by the serotype-specific WbdA mannosyltransferase. In serotype O9a, WbdA is a bifunctional α-(1→2)-, α-(1→3)-mannosyltransferase, and its counterpart in serotype O8 is trifunctional (α-(1→2), α-(1→3), and β-(1→2)). Little is known about the detailed structures or mechanisms of action of the WbdA polymerases, and here we establish that they are multidomain enzymes. WbdA(O9a) contains two separable and functionally active domains, whereas WbdA(O8) possesses three. In WbdC(O9a) and WbdB(O9a), substitution of the first Glu of the EX(7)E motif had detrimental effects on the enzyme activity, whereas substitution of the second had no significant effect on activity in vivo. Mutation of the Glu residues in the EX(7)E motif of the N-terminal WbdA(O9a) domain resulted in WbdA variants unable to synthesize O-PS. In contrast, mutation of the Glu residues in the motif of the C-terminal WbdA(O9a) domain generated an enzyme capable of synthesizing an altered O-PS repeat unit consisting of only α-(1→2) linkages. In vitro assays with synthetic acceptors unequivocally confirmed that the N-terminal domain of WbdA(O9a) possesses α-(1→2)-mannosyltransferase activity. Together, these studies form a framework for detailed structure-function studies on individual domains and a strategy applicable for dissection and analysis of other multidomain glycosyltransferases
biosynthesis, synthesis, serotype, Escherichia coli, O-antigens, serotype-specific, mannosyltransferases, WbdA(O9a), WbdC(O9a), WbdB(O9a)
NCBI PubMed ID: 22989876Publication DOI: 10.1074/jbc.M112.412577Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: cwhitfie@uoguelph.ca
Institutions: From the Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1
Methods: 13C NMR, 1H NMR, SDS-PAGE, MALDI-TOF MS, NMR-1D, genetic methods, biochemical methods, computer analysis with CASPER, bioinformatic analysis
- Article ID: 4307
Greenfield LK, Whitfield C "Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways" -
Carbohydrate Research 356 (2012) 12-24
The O-polysaccharide (O-PS; O-antigen) of bacterial lipopolysaccharides is made up of repeating units of one or more sugar residues and displays remarkable structural diversity. Despite the structural variations, there are only three strategies for O-PS assembly. The ATP-binding cassette (ABC)-transporter-dependent mechanism of O-PS biosynthesis is widespread. The Escherichia coli O9a and Klebsiella pneumoniae O2a antigens provide prototypes, which are distinguished by the fine details that link glycan polymerization and chain termination at the cytoplasmic face of the inner membrane to its export via the ABC transporter. Here, we describe the current understanding of these processes. Since glycoconjugate assembly complexes that utilize an ABC transporter-dependent pathway are widespread among the bacterial kingdom, the models described here are expected to extend beyond O-PS biosynthesis systems
Lipopolysaccharide, O-polysaccharide, ATP-binding cassette transporter, Escherichia coli O9a, Klebsiella pneumoniae O2a
NCBI PubMed ID: 22475157Publication DOI: 10.1016/j.carres.2012.02.027Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. Whitfield
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
- 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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 5143
Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" -
Natural Product Reports 35(12) (2018) 1251-1293
Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.
lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism
Publication DOI: 10.1039/C8NP00046HJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Correspondence: charles.gauthier@iaf.inrs.ca
Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
- Article ID: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
- Article ID: 5820
Naumenko OI, Zheng H, Shashkov AS, Sun Y, Senchenkova SN, Bai L, Wang J, Wang H, Li Q, Knirel YA, Xiong Y "Escherichia albertii EA046(O9) harbors two polysaccharide gene clusters for synthesis of the O-antigen by the Wzx/Wzy-dependent pathway and a mannan shared by Escherichia coli O8 by the Wzm/Wzt-dependent pathway" -
International Journal of Molecular Sciences 142 (2020) 609-614
O antigen is a polysaccharide chain of a lipopolysaccharide on the outer membrane of Gram-negative bacteria. O-antigen-based serotyping and molecular typing are widely used for epidemiological and surveillance purposes. Two polysaccharides were isolated by Sephadex G-50 gel-permeation chromatography following mild acid degradation of the lipopolysaccharide of Escherichia albertii EA046 assigned to serotype O9. The polysaccharide eluted first was considered as the O-antigen. It was composed of tetrasaccharide repeating units containing two residues of d-Man and one residue each of d-Gal and d-GlcNAc as well as glycerol phosphate. It had the following unique structure which was established by NMR spectroscopy applied to the initial and dephosphorylated polysaccharides: The polysaccharide eluted from the gel second was identified as a mannan with a → 3)-β-d-Manp-(1 → 2)-α-d-Manp-(1 → 2)-α-d-Manp-(1 → trisaccharide repeating unit. In E. albertii EA046, two polysaccharide gene clusters were found at a chromosomal locus flanked by the conserved galF gene and the histidine synthesis operon (his). They were suggested to drive the biosynthesis of the O-antigen by the Wzy/Wzy-dependent pathway and the mannan by the Wzm/Wzt-dependent pathway. The mannan shares the structure and gene cluster with a polysaccharide isolated earlier from the lipopolysaccharide of Escherichia coli O8.
Lipopolysaccharide, O-antigen, Escherichia albertii
NCBI PubMed ID: 31622726Publication DOI: 10.1016/j.ijbiomac.2019.09.135Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: Yanwen Xiong
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zigong Center for Disease Control and Prevention, Zigong, Sichuan Province, China, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Hangzhou, Zhejiang Province, China, State Key Laboratory of Infectious Disease Prevention and Control, National Institute for Communicable Disease Control and Prevention, Chinese Center for Disease Control and Prevention, Beijing, China, Anhui Provincial Center for Disease Control and Prevention, Hefei, China, Division I of Risk Assessment, China National Center for Food Safety Risk Assessment, Beijing, China
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, dephosphorylation, 31P NMR, GLC, GPC, function analysis of gene clusters
- Article ID: 6088
Knirel YA, Kenyon JJ "Biosynthesis of bacterial polysaccharides" -
Book: Polysaccharides of Microbial Origin. Biomedical Applications (2021) 453-479
The present chapter is devoted to biosynthesis pathways of various bacterial surface polysaccharides, including slime exopolysaccharides and capsular polysaccharides, as well as the O-antigen polysaccharide chains of lipopolysaccharides. The polysaccharides are extraordinarily diverse in structure and define the specificity of interaction between bacteria and their environments, including interactions with host organisms, bacteriophages, and natural predators. As such, both homopolysaccharides and heteropolysaccharides produced by bacteria have an important function in bacterial lifestyle, particularly in protection of human pathogens against the immune system response and some antimicrobials. In both gram-negative and gram-positive bacteria, biosynthesis of most cell-surface heteropolysaccharides is accomplished by the Wzy-dependent pathway, whereas some exopolysaccharides, such as a β-(1-6)-linked polymer of D-GlcpNAc called PNAG, are synthesized by the synthase-dependent pathway. For synthesis of homopolysaccharides and some heteropolysaccharides with a small (di- or tri-saccharide) repeating unit, gram-negative bacteria use the ATP-binding cassette (ABC) transporter-dependent pathway. A fourth pathway is utilized for the extracellular synthesis of several glucans and fructus by a single sucrase protein. The specific mechanisms of these pathways, including a brief view on the genetics of the polysaccharide biosynthesis, is provided.
lipopolysaccharides, capsular polysaccharides, bacteria, exopolysaccharides, gram negative bacteria, biosynthesis pathway
Publication DOI: 10.1007/978-3-030-42215-8_28Publisher: Springer
Correspondence: Y.A. Knirel
; johanna.kenyon@qut.edu.au
Editors: J.Oliveira HRRLR
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunolgy and Infection Control University of Minho, (CIIC), School of Biomedical Sciences, Queensland University of Technology, Brisbane, QLD, Australia URWPalladioL-Rom
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2. Compound ID: 1130
|
-2)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 340
Nnalue NA, Lindberg AA "O-antigenic determinants in Salmonella species of serogroup C1 are expressed in distinct immunochemical populations of chains" -
Microbiology 143(2) (1997) 641-652
The O-antigenic specificities found among Salmonellae of serogroup C1 are O:6(1),7, O:6(2),7, O:6(1),6(2),7 and O:6,7,14, as defined by classical serology. Factor O:7 is the group-wide determinant while factors O:6(1), O:6(2) and O:14 are found in some strains but not others. Strains of the O:6(2),7 specificity are subject to lysogenic conversion by phages 6(1) and 14 to the O:6(1),7 and O:6,7,14 specificities, respectively. To further delineate antigenic complexity and serological relationships among strains of this serogroup monoclonal antibodies (mAbs) were generated against the O:6(1),6(2),7 polysaccharide of Salmonella thompson. Five mAbs of either the O:6(1) or O:6(2) specificities did not bind O:6,7,14 strains or LPS, showing that the O:6 determinant in these strains is neither O:6(1) nor O:6(2). Thus antigenic conversion of O:6(2),7 strains by phage 14 is accompanied by addition of O:14 as well as loss of O:6(2). Three mAbs which demonstrated group-wide reactivity, and were thus specific for O:7, recognized clearly by separable epitopes hereby defined as sub-specificities, O:7(1), O:7(2) and O:7(3). Immunoblotting of mAbs against electrophoretically resolved LPS showed that factors O:6(1) and O:6(2) are expressed only in LPS molecules of high molecular mass whereas O:7(2) and O:7(3) are expressed only in relatively low-molecular-mass chains. These results are consistent with the expression of different antigenic determinants in structurally distinct subpopulations of O chains. The implications of the existence of distinct subpopulation of chains is that the published structure of the O:6,7 repeat unit is not fully representative of the O-antigenic structure of this group
Salmonella LPS, LPS epitopes, O-antigenic complexity, O-antigen populations, antigenic conversionchain
NCBI PubMed ID: 9043141Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Department of Medical Microbiology, Faculty of Medicine & Health Sciences, United Arab Emirates University, PO Box 17666, Al Ain, United Arab Emirates, Karolinska Institute, Department of Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge Hospital, S-14186, Huddinge, Sweden
Methods: SDS-PAGE, ELISA, immunoblotting
- 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 2100
Lindberg B, Leontein K, Lindquist U, Svenson SB, Wrangsell G, Dell A, Rogers M "Structural studies of the O-antigen polysaccharide of Salmonella thompson, serogroup C1 (6,7)" -
Carbohydrate Research 174 (1988) 313-322
The structure of the O-antigen polysaccharide of Salmonella thompson, serogroup C1 (6,7) has been investigated mainly by methylation analysis, n.m.r. spectroscopy, specific degradations by a phage-associated enzyme, N-deacetylation-deamination, and f.a.b.-m.s. It is concluded that the structure involves the following repeating unit. (formula; see text) There are two populations of chains, with and without α-D-glucopyranosyl groups, 3-linked to an α-D-Manp residue, and only the latter type is hydrolysed by the phage enzyme. The alpha linkage of the third Manp residue is cleaved by the O14 phage enzyme. The structure, with or without the α-D-glucopyranosyl group, represents the biological repeating-unit.
NCBI PubMed ID: 3378232Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden
Methods: 13C NMR, 1H NMR, FAB-MS
- Article ID: 3847
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- 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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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3. Compound ID: 1131
|
a-D-Glcp-(1-3)-+
|
-2)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 340
Nnalue NA, Lindberg AA "O-antigenic determinants in Salmonella species of serogroup C1 are expressed in distinct immunochemical populations of chains" -
Microbiology 143(2) (1997) 641-652
The O-antigenic specificities found among Salmonellae of serogroup C1 are O:6(1),7, O:6(2),7, O:6(1),6(2),7 and O:6,7,14, as defined by classical serology. Factor O:7 is the group-wide determinant while factors O:6(1), O:6(2) and O:14 are found in some strains but not others. Strains of the O:6(2),7 specificity are subject to lysogenic conversion by phages 6(1) and 14 to the O:6(1),7 and O:6,7,14 specificities, respectively. To further delineate antigenic complexity and serological relationships among strains of this serogroup monoclonal antibodies (mAbs) were generated against the O:6(1),6(2),7 polysaccharide of Salmonella thompson. Five mAbs of either the O:6(1) or O:6(2) specificities did not bind O:6,7,14 strains or LPS, showing that the O:6 determinant in these strains is neither O:6(1) nor O:6(2). Thus antigenic conversion of O:6(2),7 strains by phage 14 is accompanied by addition of O:14 as well as loss of O:6(2). Three mAbs which demonstrated group-wide reactivity, and were thus specific for O:7, recognized clearly by separable epitopes hereby defined as sub-specificities, O:7(1), O:7(2) and O:7(3). Immunoblotting of mAbs against electrophoretically resolved LPS showed that factors O:6(1) and O:6(2) are expressed only in LPS molecules of high molecular mass whereas O:7(2) and O:7(3) are expressed only in relatively low-molecular-mass chains. These results are consistent with the expression of different antigenic determinants in structurally distinct subpopulations of O chains. The implications of the existence of distinct subpopulation of chains is that the published structure of the O:6,7 repeat unit is not fully representative of the O-antigenic structure of this group
Salmonella LPS, LPS epitopes, O-antigenic complexity, O-antigen populations, antigenic conversionchain
NCBI PubMed ID: 9043141Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Department of Medical Microbiology, Faculty of Medicine & Health Sciences, United Arab Emirates University, PO Box 17666, Al Ain, United Arab Emirates, Karolinska Institute, Department of Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge Hospital, S-14186, Huddinge, Sweden
Methods: SDS-PAGE, ELISA, immunoblotting
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4. Compound ID: 1132
|
a-Abe-(1-3)-+ a-D-Glcp2Ac-(1-3)-+
| |
-4)-b-L-Rhap2Ac-(1-2)-b-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_164479,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_61,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 340
Nnalue NA, Lindberg AA "O-antigenic determinants in Salmonella species of serogroup C1 are expressed in distinct immunochemical populations of chains" -
Microbiology 143(2) (1997) 641-652
The O-antigenic specificities found among Salmonellae of serogroup C1 are O:6(1),7, O:6(2),7, O:6(1),6(2),7 and O:6,7,14, as defined by classical serology. Factor O:7 is the group-wide determinant while factors O:6(1), O:6(2) and O:14 are found in some strains but not others. Strains of the O:6(2),7 specificity are subject to lysogenic conversion by phages 6(1) and 14 to the O:6(1),7 and O:6,7,14 specificities, respectively. To further delineate antigenic complexity and serological relationships among strains of this serogroup monoclonal antibodies (mAbs) were generated against the O:6(1),6(2),7 polysaccharide of Salmonella thompson. Five mAbs of either the O:6(1) or O:6(2) specificities did not bind O:6,7,14 strains or LPS, showing that the O:6 determinant in these strains is neither O:6(1) nor O:6(2). Thus antigenic conversion of O:6(2),7 strains by phage 14 is accompanied by addition of O:14 as well as loss of O:6(2). Three mAbs which demonstrated group-wide reactivity, and were thus specific for O:7, recognized clearly by separable epitopes hereby defined as sub-specificities, O:7(1), O:7(2) and O:7(3). Immunoblotting of mAbs against electrophoretically resolved LPS showed that factors O:6(1) and O:6(2) are expressed only in LPS molecules of high molecular mass whereas O:7(2) and O:7(3) are expressed only in relatively low-molecular-mass chains. These results are consistent with the expression of different antigenic determinants in structurally distinct subpopulations of O chains. The implications of the existence of distinct subpopulation of chains is that the published structure of the O:6,7 repeat unit is not fully representative of the O-antigenic structure of this group
Salmonella LPS, LPS epitopes, O-antigenic complexity, O-antigen populations, antigenic conversionchain
NCBI PubMed ID: 9043141Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Department of Medical Microbiology, Faculty of Medicine & Health Sciences, United Arab Emirates University, PO Box 17666, Al Ain, United Arab Emirates, Karolinska Institute, Department of Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge Hospital, S-14186, Huddinge, Sweden
Methods: SDS-PAGE, ELISA, immunoblotting
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5. Compound ID: 1234
|
a-Tyvp-(1-6)-+
|
-3)-a-D-Manp-(1-3)-b-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_139421,IEDB_140116,IEDB_141584,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_885822,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1821
Gorshkova RP, Zubkov VA, Isakov VV, Ovodov YS "Studies on the lipopolysaccharide of Yersinia pseudotuberculosis serotype IVA" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 9(10) (1983) 1401-1407
The comparative studied on lipopolysaccharides from Yersinia pseudotuberculosis IVA serovar, strains 32 and 31D, have been conducted. The identity of the lipopolysaccharides isolated from these strains has been shown. The structural pattern of the repeating unit of the O-specific side chain of the lipopolysaccharide has been suggested: (Formula: see text)
NCBI PubMed ID: 6207839Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Sciences Center, Academy of Sciences of the USSR, Vladivostok
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6. Compound ID: 4497
|
a-D-Glcp-(1-3)-+
|
-2)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1715
Di Fabio JL, Perry MB, Brisson JR "Structure of the antigenic O-polysaccharide of the lipopolysaccharide produced by Salmonella eimsbuettel" -
Biochemistry and Cell Biology 66 (1988) 107-115
The smooth lipopolysaccharide produced by Salmonella eimsbuttel, which had the O:6, O:7, and O:14 antigenic factors defined in the Kauffmann-White classification, was shown by sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis, composition analysis, methylation, periodate oxidation, deamination, and 1H and 13C nuclear magnetic resonance studies to contain a high molecular weight O-chain polysaccharide composed of D-mannose (four parts), D-glucose (one part), and 2-acetamido-2-deoxy-D-glucose (one part). It was a branched polymer of a repeating hexasaccharide unit having the structure (formula; see text).
NCBI PubMed ID: 2453206Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Institutions: Division of Biological Sciences, National Research Council, Ottawa, Ont., Canada
- 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3847
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- 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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Expand this compound
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7. Compound ID: 4504
|
a-D-Glcp-(1-3)-+
|
-2)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1721
Di Fabio JL, Brisson JR, Perry MB "Structure of the lipopolysaccharide antigenic O-chain produced by Salmonella livingstone (O:6,7)" -
Biochemistry and Cell Biology 67(6) (1989) 278-280
The lipopolysaccharide produced by Salmonella livingstone (O:6,7) was composed of an antigenic O-polysaccharide which was shown by composition, methylation analysis, and high resolution nuclear magnetic resonance studies to be a high molecular weight polymer containing D-glucose, 2-acetamido-2-deoxy-D-glucose, and D-mannose residues (1:1:4) composed in a repeating hexasaccharide unit having the structure: (formula; see text)
NCBI PubMed ID: 2476161Publication DOI: 10.1139/o89-041Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ont.
- 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 2100
Lindberg B, Leontein K, Lindquist U, Svenson SB, Wrangsell G, Dell A, Rogers M "Structural studies of the O-antigen polysaccharide of Salmonella thompson, serogroup C1 (6,7)" -
Carbohydrate Research 174 (1988) 313-322
The structure of the O-antigen polysaccharide of Salmonella thompson, serogroup C1 (6,7) has been investigated mainly by methylation analysis, n.m.r. spectroscopy, specific degradations by a phage-associated enzyme, N-deacetylation-deamination, and f.a.b.-m.s. It is concluded that the structure involves the following repeating unit. (formula; see text) There are two populations of chains, with and without α-D-glucopyranosyl groups, 3-linked to an α-D-Manp residue, and only the latter type is hydrolysed by the phage enzyme. The alpha linkage of the third Manp residue is cleaved by the O14 phage enzyme. The structure, with or without the α-D-glucopyranosyl group, represents the biological repeating-unit.
NCBI PubMed ID: 3378232Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden
Methods: 13C NMR, 1H NMR, FAB-MS
- Article ID: 3847
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- 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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Expand this compound
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8. Compound ID: 4681
|
a-D-Glcp-(1-3)-+
|
-2)-b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- 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: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3847
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- 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_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Expand this compound
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9. Compound ID: 6074
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
Expand this compound
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10. Compound ID: 6081
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
Expand this compound
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11. Compound ID: 6083
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_858578,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
Expand this compound
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12. Compound ID: 6086
|
SUG-(1-5)-+
|
D-Manp-(1-2)-D-Manp-(1-5)-D-Araf-(1-2)-D-Araf-(1-3)-D-Araf |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
Expand this compound
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13. Compound ID: 6087
|
SUG-(1-3)-+
|
D-Manp-(1-2)-D-Manp-(1-5)-D-Araf-(1-2)-D-Araf-(1-5)-D-Araf |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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14. Compound ID: 6089
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_858578,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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15. Compound ID: 6193
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b-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1-3)-b-D-GlcpNAc |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_151531,IEDB_152206,IEDB_164479,IEDB_2278480,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2769
Grossman N, Svenson SB, Leive L, Lindberg AA "Salmonella O-antigen-specific oligosaccharide-octyl conjugates activate complement via the alternative pathway at different rates depending on the structure of the O antigen" -
Molecular Immunology 27 (1990) 859-865
Artificial Salmonella serogroup B, D or Cl-specific glycolipids were prepared by covalently linking oligosaccharides corresponding to two O-antigen repeating units, obtained by phage enzyme hydrolysis of native O-antigenic polysaccharides, to octyl residues. Sheep erythrocytes coated with the artificial glycolipids were studied for their ability to consume C3, when incubated in C4- deficient guinea pig serum. Salmonella C1 (0-6,7) glycolipid-coated erythrocytes consumed C3 40% more efficiently than Salmonella D (0-9,12) glycolipid-coated erythrocytes, and 10-times more efficiently than Salmonella B (0-4,12) glycolipid-coated erythrocytes. These results resemble C3 consumption by Salmonella C1, D, and B cells and by sheep erythrocytes coated with purified lipopolysaccharides of these O-specificities. The results prove directly that in a particulate system C3 activation via the alternative pathway depends on the structural properties of the O-antigenic side chain. Structures as small as octasaccharides, or as two O-antigenic repeating units, are sufficient for triggering C3 activation, but the magnitude of activation depends on the nature of the monosaccharides. Apparently, neither the core oligosaccharide nor Lipid A of lipopolysaccharide are required for C3 activation via the alternative pathway
NCBI PubMed ID: 1699120Journal NLM ID: 7905289Publisher: Elsevier
Institutions: Laboratory of Structural Biology, National Institute of Arthritis, Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
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