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1. Compound ID: 906
Structure type: homopolymer
Trivial name: 6-deoxy-heptan CPS
Compound class: CPS, O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 260
Ho M, Schollaardt T, Smith MD, Perry MB, Brett PJ, Chaowagul W, Bryan LE "Specificity and functional activity of anti-Burkholderia pseudomallei polysaccharide antibodies" -
Infection and Immunity 65(9) (1997) 3648-3653
The lipopolysaccharide (LPS) of Burkholderia pseudomallei, the causative agent of melioidosis, consists of two O-antigenic polysaccharides designated O-PS I and O-PS II. In this study, the O-PS specificity and functional activity of a protective polyclonal antiserum and an immunoglobulin M (IgM) monoclonal antibody were determined. The polyclonal antiserum recognized both O-PS I and O-PS II, while the monoclonal antibody was O-PS II specific. Both mediated phagocytic killing of B. pseudomallei by polymorphonuclear leukocytes. Patients acutely infected with B. pseudomallei also produced antibodies to the two O-PSs, but these antibodies were not produced by asymptomatic individuals from an area of endemicity who were seropositive by an indirect hemagglutination test using sonicated heat-killed whole organisms as antigen. IgM antibodies were detected only in patients with localized infection. IgG antibodies were detected in all acutely infected patients, but there was no significant difference in antibody levels among patients with localized infection, patients who survived septicemic illness, and patients who died from septicemic illness. Further analysis of the IgG response revealed production of IgG1 and IgG2 antibodies by all patient groups, while an IgG3 response was seen only in survivors of septicemic infection. IgG4 was not detectable even when a fivefold-lower serum dilution was used. Patient sera also mediated phagocytic killing by polymorphonuclear leukocytes, and the killing effect was enhanced by complement. These results suggest that antibodies to the LPS O-polysaccharides of B. pseudomallei are protective by promoting phagocytic killing. The antibodies develop during human infection and may facilitate clearance of the organisms, as seen in a diabetic rat model of B. pseudomallei infection.
antibodies, Burkholderia pseudomallei, specificity, polysaccharides, functional activity
NCBI PubMed ID: 9284132Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology and Infectious Diseases, University of Calgary, Calgary, Alberta, and Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, Faculty of Tropical Medicine, Mahidol University, Bangkok, and Department of Medicine, Sappasitprasong Hospital, Ubol Ratchatani, Thailand, Nuffield Department of Clinical Medicine, John Radcliffe Hospital, Oxford University, Oxford, United Kingdom.
Methods: serological methods
- Article ID: 830
Isshiki Y, Matsuura M, Dejsirilert S, Ezaki T, Kawahara K "Separation of 6-deoxy-heptane from a smooth-type lipopolysaccharide preparation of Burkholderia pseudomallei" -
FEMS Microbiology Reviews 199 (2001) 21-25
Smooth-type lipopolysaccharide (LPS) of Burkholderia pseudomallei has been reported to contain two kinds of O-antigenic polysaccharides, a 1,3-linked homopolymer of 6-deoxy-heptose and a polymer with a repeating unit of →3)-glucose-(1→3)-6-deoxytalose-(1→ with O-acetyl or O-methyl modifications. A LPS preparation containing these two polysaccharides was separated by gelpermeation chromatography in this study. Chemical analysis of the separated fractions revealed the 6-deoxy-heptane to be a polysaccharide without a lipid portion and the polymer of glucose and 6-deoxy-talose to be an O-antigenic polysaccharide of the LPS. This result was further supported by the assay of these polysaccharide molecules for macrophage activation activity. The 6-deoxy-heptane showed no macrophage activation, indicating that this polysaccharide was not the LPS, but one of the capsular polysaccharides of B. pseudomallei.
Lipopolysaccharide, structure, Burkholderia, Burkholderia pseudomallei, chemical, isolation, preparation, separation, melioidosis
NCBI PubMed ID: 11356562Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: kawahara-k@kitasato.or.jp
Institutions: Department of Bacteriology, The Kitasato Institute, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8642, Japan, Department of Microbiology, Jichi Medical School, 3311-1 Yakushiji, Minamikawachi-machi, Tochigi 329-0498, Japan, National Institute of Health, Nonthaburi 11000, Thailand, Department of Microbiology, Gifu University School of Medicine, 40 Tsukasa-machi, Gifu 500-8705, Japan
Methods: SDS-PAGE, GLC, GPC
- Article ID: 1099
Perry MB, MacLean LL, Schollaardt T, Bryan LE, Ho M "Structural characterization of the lipopolysaccharide O antigens of Burkholderia pseudomallei" -
Infection and Immunity 63(9) (1995) 3348-3352
A serologically typical strain of Burkholderia pseudomallei (strain 304b) was found to produce two S-type lipopolysaccharides (LPS) differing in the chemical structures of their O-polysaccharide (O-PS) components. Structural analysis revealed that one O-antigenic polysaccharide (O-PS I) is an unbranched high-molecularweight polymer of 1,3-linked 2-O-acetyl-6-deoxy-β-D-manno-heptopyranose residues. The other LPS O antigen (O-PS II) is an unbranched polymer of repeating disaccharide units having the structure →3)-β-D-glucopyranose-(1→3)-6-deoxy-α-L-talopyranose-(1→ in which ca. 33% of the L6dTalp residues bear 2-O-methyl and 4-O-acetyl substituents while the other L6dTalp residues carry only 2-O-acetyl substituents. Analysis of a serologically atypical strain of B. pseudomallei (strain 824a) produced a single LPS O-PS which was chemically identical to the 6-deoxy-D-manno-heptan O-PS I. The production of two distinct LPS raises the interesting question of their relative immunogenicities and consequently their relative importance for diagnostic serology and for the possible development of conjugate vaccines.
Lipopolysaccharide, antigen, LPS, structural, characterization, Burkholderia, O-antigen, O antigen, Pseudomonas, antigens, Burkholderia pseudomallei, O antigens, O-antigens, Pseudomonas pseudomallei
NCBI PubMed ID: 7543882Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A OR6,1, Department of Microbiology and Infectious Diseases, Health Science Centre, Calgary, Alberta, Canada T2N 4N12
Methods: NMR-2D, NMR
- Article ID: 1415
DeShazer D, Waag DM, Fritz DL, Woods DE "Identification of a Burkholderia mallei polysaccharide gene cluster by subtractive hybridization and demonstration that the encoded capsule is an essential virulence determinant" -
Microbial Pathogenesis 30(5) (2001) 253-269
Little is known about the virulence factors of Burkholderia mallei, the etiologic agent of glanders. We employed subtractive hybridization to identify genetic determinants present in B. mallei but not in Burkholderia thailandensis, a non-pathogenic soil microbe. Three subtractive hybridization products were mapped to a genetic locus encoding proteins involved in the biosynthesis, export and translocation of a capsular polysaccharide. We identified an insertion sequence (IS 407 A) at one end of the capsule gene cluster and demonstrated that it was functional in B. mallei. Mutations were introduced in the B. mallei capsular gene cluster and the corresponding mutants were examined for their reactivity with antibodies raised against Burkholderia pseudomallei surface polysaccharides by immunoblotting and ELISA. Immunogold electron microscopy demonstrated the presence of a capsule on the surface of B. mallei ATCC 23344 (parental strain) but not on B. mallei DD3008 (capsule mutant) or B. thailandensis. Surprisingly, B. thailandensis also harboured a portion of the capsule gene cluster. ATCC 23344 was highly virulent in hamsters and mice, but DD3008 was avirulent in both animal models. The results presented here demonstrate that the capsular polysaccharide of B. mallei is required for production of disease in two animal models of glanders infection and is a major virulence factor.
Burkholderia pseudomallei, melioidosis, glanders, pathogenesis and animal model
NCBI PubMed ID: 11373120Journal NLM ID: 8606191Publisher: Academic Press
Correspondence: david.deshazer@amedd.army.mil
Institutions: U.S.Army Medical Research Institute of Infectious Diseases,Fort Detrick, Maryland, USA
- Article ID: 1416
DeShazer D, Brett PJ, Woods DE "The type II O-antigenic polysaccharide moiety of Burkholderia pseudomallei lipopolysaccharide is required for serum resistance and virulence" -
Molecular Microbiology 30(5) (1998) 1081-1100
Melioidosis, an infection caused by the gram-negative bacterial pathogen Burkholderia pseudomallei, is endemic in south-east Asia and northern Australia. Acute septicaemic melioidosis is a major cause of morbidity and mortality, especially in north-east Thailand. B. pseudomallei is highly resistant to the bactericidal activity of normal human serum (NHS), and we have found that B. pseudomallei 1026b multiplies in 10-30% NHS. We developed a simple screen for the identification of serum-sensitive mutants based on this novel phenotype. Approximately 1200 Tn5-OT182 mutants were screened, and three serum-sensitive mutants were identified. The type II O-antigenic polysaccharide (O-PS) moiety of lipopolysaccharide was not present in the serum-sensitive mutants. A representative serum-sensitive mutant, SRM117, was killed by the alternative pathway of complement and was less virulent than 1026b in three animal models of melioidosis. The Tn5-OT182 integrations in the serum-sensitive mutants were physically linked on the B. pseudomallei chromosome, and further genetic analysis of this locus revealed a cluster of 15 genes required for type II O-PS production. The proteins encoded by these genes were similar to proteins involved in bacterial polysaccharide biosynthesis. The results presented here demonstrate that type II O-PS is essential for B. pseudomallei serum resistance and virulence.
Lipopolysaccharide, virulence, Burkholderia, O-antigenic polysaccharide, Burkholderia pseudomallei, serum resistance, melioidosis
NCBI PubMed ID: 9988483Publication DOI: 10.1046/j.1365-2958.1998.01139.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: woods@acs.ucalgary.ca
Institutions: University 0f Calgary Health Sciences Centre,Calgary,Canada
- Article ID: 1557
Reckseidler-Zenteno SL, DeVinney R, Woods DE "The capsular polysaccharide of Burkholderia pseudomallei contributes to survival in serum by reducing complement factor C3b deposition" -
Infection and Immunity 73(2) (2005) 1106-1115
Burkholderia pseudomallei produces an extracellular polysaccharide capsule -3)-2-O-acetyl-6-deoxy-β-D-manno-heptopyranose-(1- which has been shown to be an essential virulence determinant. The addition of purified capsule was shown to increase the virulence of a capsule mutant strain in the Syrian hamster model of acute melioidosis. An increase in the number of wild-type B. pseudomallei cells in the blood was seen by 48 h, while the number of capsule mutant cells in the blood declined by 48 h. Capsule expression was shown to be induced in the presence of serum using a lux reporter fusion to the capsule gene wcbB. The addition of purified B. pseudomallei capsule to serum bactericidal assays increased the survival of B. pseudomallei SLR5, a serum-sensitive strain, by 1,000-fold in normal human serum. Capsule production by B. pseudomallei contributed to reduced activation of the complement cascade by reducing the levels of complement factor C3b deposition. An increase in phagocytosis of the capsule mutant compared to the wild type was observed in the presence of normal human serum. These results suggest that the production of this capsule contributes to resistance to phagocytosis by reducing C3b deposition on the surface of the bacterium, thereby contributing to the persistence of bacteria in the blood of the infected host. Continued studies to characterize this capsule are essential for understanding the pathogenesis of B. pseudomallei infections and the development of preventive strategies for treatment of this disease
Pathogenesis, blood, disease, expression, gene, host, human, metabolism, microbiology, strain, Non-U.S.Gov't, virulence, capsular, polysaccharide, Burkholderia, cell, capsular polysaccharide, type, activation, animal, factor, induced, infection, level, wild type, Burkholderia pseudomallei, infectious disease, bacteria, mutant, glycosyltransferases, extracellular polysaccharide, polysaccharides, production, reduced, surface, capsule, Infectious, treatment, purified, determinant, extracellular, reducing, Disease Models, resistance, serum, cells, bactericidal, phagocytosis, human serum, acute, Bacterial Capsules, assay, model, melioidosis, characterize, development, complement, Animals, Research Support, survival, Complement 3b, fusion, hamster, Hamsters, infected, persistence, reporter
NCBI PubMed ID: 15664954Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology and Infectious Diseases, University of Calgary Health Sciences Center, 3330 Hospital Drive NW, Calgary, Alberta, Canada T2N 4N1
Methods: serological methods, genetic methods
- 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: 2228
Knirel YA, Paramonov NA, Shashkov AS, Kochetkov NK, Yarullin RG, Farber SM, Efremenko VI "Structure of the polysaccharide chains of Pseudomonas pseudomallei lipopolysaccharides" -
Carbohydrate Research 233 (1992) 185-193
The pathogenic bacterium Pseudomonas pseudomallei strain 57576 produces two partially O-acetylated O-antigenic polysaccharides (PS-I and PS-II). Methylation analysis and 1H and 13C NMR spectroscopy, including NOE experiments, showed PS-I to have the structure [formula: see text] and PS-II to have the structure [formula: see text] where 6dmanHep is the unusual higher sugar 6-deoxy-D-manno-heptose. PS-II is produced also by P. pseudomallei strains 100 and 110, and PS-I and O-deacetylated PS-II by strain 97.
Lipopolysaccharide, O-antigen, NMR spectroscopy, O-polysaccharide, Pseudomonas pseudomallei, 6-deoxy-D-manno-heptose
NCBI PubMed ID: 1280183Publication DOI: 10.1016/S0008-6215(00)90930-3Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Antiplague Research Institute, Health Ministry, Volgograd, Russia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, paper chromatography, de-O-acetylation
- Article ID: 3582
Parthasarathy N, Saksena R, Kovác P, DeShazer D, Peacock SJ, Wuthiekanun V, Heine HS, Friedlander AM, Cote CK, Welkos SL, Adamovicz JJ, Bavari S, Waag DM "Application of carbohydrate microarray technology for the detection of Burkholderia pseudomallei, Bacillus anthracis and Francisella tularensis antibodies" -
Carbohydrate Research 343(16) (2008) 2783-2788
We developed a microarray platform by immobilizing bacterial 'signature' carbohydrates onto epoxide modified glass slides. The carbohydrate microarray platform was probed with sera from non-melioidosis and melioidosis (Burkholderia pseudomallei) individuals. The platform was also probed with sera from rabbits vaccinated with Bacillus anthracis spores and Francisella tularensis bacteria. By employing this microarray platform, we were able to detect and differentiate B. pseudomallei, B. anthracis and F. tularensis antibodies in infected patients, and infected or vaccinated animals. These antibodies were absent in the sera of nai ve test subjects. The advantages of the carbohydrate microarray technology over the traditional indirect hemagglutination and microagglutination tests for the serodiagnosis of melioidosis and tularemia are discussed. Furthermore, this array is a multiplex carbohydrate microarray for the detection of all three biothreat bacterial infections including melioidosis, anthrax and tularemia with one, multivalent device. The implication is that this technology could be expanded to include a wide array of infectious and biothreat agents
Bacillus anthracis (anthrax), Burkholderia pseudomallei (melioidosis), carbohydrate microarray, Francisella tularensis (tularemia), Serum antibodies
NCBI PubMed ID: 18558401Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: N. Parthasarathy
Institutions: Bacteriology Division, United States Army Medical Research Institute of Infectious Diseases, Frederick, MD, USA
Methods: serological methods
- Article ID: 3607
Parthasarathy N, DeShaser D, Peacock SJ, Wuthiekanun V, England MJ, Norris SL, Waag DM "Application of polysaccharide microarray technology for the serodiagnosis of Burkholderia pseudomallei infection (melioidosis) in humans" -
Journal of Carbohydrate Chemistry 27 (2008) 32-40
Burkholderia pseudomallei is the causative agent of melioidosis, a bacterial infection endemic in tropical regions including southeast Asia and northern Australia. B. pseudomallei contains structurally unique polysaccharides (capsular polysaccharide and O 2 antigen saccharides of lipopolysaccharide). A polysaccharide microarray platform was developed by immobilizing these polysaccharides onto glass slides. Employing this microarray, we were able to demonstrate the presence of antibodies to these polysaccharide antigens in the sera of melioidosis patients, but not in serum from nonmelioidosis human subjects. The advantages of this polysaccharide microarray technology over the conventional tests for the serodiagnosis of melioidosis are discussed.
Burkholderia pseudomallei, melioidosis, polysaccharide microarray, serodiagnosis
Publication DOI: 10.1080/07328300802030761Journal NLM ID: 8218151Publisher: Marcel Dekker
Correspondence: parthasarathy@us.army.mil
Institutions: Bacteriology Division, United States Army Medical Research Institute of Infectious Diseases, Frederick, MD, USA
Methods: serological methods
- Article ID: 4112
Shilova NV, Navakouski MJ, Huflejt M, Kuehn A, Grunow R, Blixt O, Bovin NV "Changes in the repertoire of natural antibodies caused by immunization with bacterial antigens" -
Biochemistry (Moscow) 76(7) (2011) 862-866
The repertoire of natural anti-glycan antibodies in naive chickens and in chickens immunized with bacteria Burkholderia mallei, Burkholderia pseudomallei, and Francisella tularensis as well as with peptides from an outer membrane protein of B. pseudomallei was studied. A relatively restricted pattern of natural antibodies (first of all IgY against bacterial cell wall peptidoglycan fragments, L-Rha, and core N-acetyllactosamine) shrank and, moreover, the level of detectable antibodies decreased as a result of immunization.
Burkholderia pseudomallei, Francisella tularensis, bacterial polysaccharides, Burkholderia mallei, natural antibodies
NCBI PubMed ID: 21999548Publication DOI: 10.1134/S0006297911070170Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: bovin@carbohydrate.ru
Institutions: Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. MiklukhoMaklaya 16/10, 117997 Moscow, Russia
Methods: serological methods, immunization
- Article ID: 4281
Burtnick MN, Heiss C, Roberts RA, Schweizer HP, Azadi P, Brett PJ "Development of capsular polysaccharide-based glycoconjugates for immunization against melioidosis and glanders" -
Frontiers in Cellular and Infection Microbiology 2 (2012) 108
Burkholderia pseudomallei and Burkholderia mallei, the etiologic agents of melioidosis and glanders, respectively, cause severe disease in humans and animals and are considered potential agents of biological warfare and terrorism. Diagnosis and treatment of infections caused by these pathogens can be challenging and, in the absence of chemotherapeutic intervention, acute disease is frequently fatal. At present, there are no human or veterinary vaccines available for immunization against these emerging/re-emerging infectious diseases. One of the long term objectives of our research, therefore, is to identify and characterize protective antigens expressed by B. pseudomallei and B. mallei and use them to develop efficacious vaccine candidates. Previous studies have demonstrated that the 6-deoxy-heptan capsular polysaccharide (CPS) expressed by these bacterial pathogens is both a virulence determinant and a protective antigen. Consequently, this carbohydrate moiety has become an important component of the various subunit vaccines that we are currently developing in our laboratory. In the present study, we describe a reliable method for isolating CPS antigens from O-polysaccharide (OPS) deficient strains of B. pseudomallei; including a derivative of the select agent excluded strain Bp82. Utilizing these purified CPS samples, we also describe a simple procedure for covalently linking these T-cell independent antigens to carrier proteins. In addition, we demonstrate that high titer IgG responses can be raised against the CPS component of such constructs. Collectively, these approaches provide a tangible starting point for the development of novel CPS-based glycoconjugates for immunization against melioidosis and glanders.
capsular polysaccharide, immunization, Burkholderia pseudomallei, vaccine, glycoconjugate, Burkholderia mallei
NCBI PubMed ID: 22912938Publication DOI: 10.3389/fcimb.2012.00108Journal NLM ID: 101585359Publisher: Lausanne: Frontiers Media SA
Correspondence: pbrett@southalabama.edu
Institutions: Department of Microbiology and Immunology, University of South Alabama Mobile, AL, USA
Methods: 13C NMR, 1H NMR, PCR, Western blotting, genetic methods, conjugation
- 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: 4313
Heiss C, Burtnick MN, Wang Z, Azadi P, Brett PJ "Structural analysis of capsular polysaccharides expressed by Burkholderia mallei and Burkholderia pseudomallei" -
Carbohydrate Research 349 (2012) 90-94
Capsular polysaccharides (CPSs) were isolated from O-polysaccharide deficient strains of Burkholderia mallei and Burkholderia pseudomallei using a modified hot phenol/water extraction procedure. Glycosyl composition, methylation, MALDI-TOF MS analyses as well as (1)H NMR spectroscopy including COSY, TOCSY, NOESY, HMBC and HSQC experiments identified the presence of two distinct CPS antigens in the samples exhibiting the following structures: This study confirms the ability of B. mallei to express a 6-deoxy-heptan CPS and represents the first report of a mannan CPS being expressed by these bacterial pathogens.
structure, capsular polysaccharide, Burkholderia pseudomallei, Burkholderia mallei, protective antigen NMR
NCBI PubMed ID: 22221792Publication DOI: 10.1016/j.carres.2011.12.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. Heiss
; M.N. Burtnick
Institutions: Complex Carbohydrate Research Center, The University of Georgia, Athens, GA 30602, USA
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, MALDI-TOF MS, composition analysis, NMR-1D
- Article ID: 4732
Tamigney Kenfack M, Bleriot Y, Gauthier C "Intramolecular aglycon delivery enables the synthesis of 6-deoxy-b-D-manno-heptosides as fragments of Burkholderia pseudomallei and Burkholderia mallei capsular polysaccharide" -
Journal of Organic Chemistry 79(10) (2014) 4615-4634
Burkholderia pseudomallei and Burkholderia mallei are potential bioterrorism agents. They express the same capsular polysaccharide (CPS), a homopolymer featuring an unusual [→3)-2-O-acetyl-6-deoxy-β-D-manno-heptopyranosyl-(1→] as the repeating unit. This CPS is known to be one of the main targets of the adaptive immune response in humans and therefore represents a crucial subunit candidate for vaccine development. Herein, the stereoselective synthesis of mono- and disaccharidic fragments of the B. pseudomallei and B. mallei CPS repeating unit is reported. The synthesis of 6-deoxy-β-D-manno-heptosides was investigated using both inter- and intramolecular glycosylation strategies from thio-manno-heptose that was modified with 2-naphthylmethyl (NAP) at C2. We show here that NAP-mediated intramolecular aglycon delivery (IAD) represents a suitable approach for the stereocontrolled synthesis of 6-deoxy-β-D-manno-heptosides without the need for rigid 4,6-O-cyclic protection of the sugar skeleton. The IAD strategy is highly modular, as it can be applied to structurally diverse acceptors with complete control of stereoselectivity. Problematic hydrogenation of the acetylated disaccharides was overcome by using a microfluidic continuous flow reactor.
synthesis, capsular polysaccharide, Burkholderia pseudomallei, Burkholderia mallei
NCBI PubMed ID: 24786555Publication DOI: 10.1021/jo500640nJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: charles.gauthier@univ-poitiers.fr
Institutions: Université de Poitiers, Institut de Chimie IC2MP, UMR-CNRS 7285, Équipe Synthèse Organique, 4 rue Michel Brunet, 86073 Poitiers, France
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, glycosylation, ESI-TOF-MS
- Article ID: 4858
Marchetti R, Dillon MJ, Burtnick MN, Hubbard MA, Kenfack MT, Blériot Y, Gauthier C, Brett PJ, Aucoin DP, Lanzetta R, Silipo A, Molinaro A "Burkholderia pseudomallei Capsular Polysaccharide Recognition by a Monoclonal Antibody Reveals Key Details toward a Biodefense Vaccine and Diagnostics against Melioidosis" -
ACS Chemical Biology 10(10) (2015) 2295-2302
Burkholderia pseudomallei is the bacterium responsible for melioidosis, an infectious disease with high mortality rates. Since melioidosis is a significant public health concern in endemic regions and the organism is currently classified as a potential biothreat agent, the development of effective vaccines and rapid diagnostics is a priority. The capsular polysaccharide (CPS) expressed by B. pseudomallei is a highly conserved virulence factor and a protective antigen. Because of this, CPS is considered an attractive antigen for use in the development of both vaccines and diagnostics. In the present study, we describe the interactions of CPS with the murine monoclonal antibody (mAb) 4C4 using a multidisciplinary approach including organic synthesis, molecular biology techniques, surface plasmon resonance, and nuclear magnetic spectroscopy. Using these methods, we determined the mode of binding between mAb 4C4 and native CPS or ad hoc synthesized capsular polysaccharide fragments. Interestingly, we demonstrated that the O-acetyl moiety of CPS is essential for the interaction of the CPS epitope with mAb 4C4. Collectively, our results provide important insights into the structural features of B. pseudomallei CPS that enable antibody recognition that may help the rational design of CPS-based vaccine candidates. In addition, our findings confirm that the mAb 4C4 is suitable for use in an antibody-based detection assay for diagnosis of B. pseudomallei infections.
synthesis, antigen, epitope, monoclonal antibodies, capsular polysaccharide, MAb, Burkholderia pseudomallei, vaccines, virulence factor, Surface Plasmon Resonance, monoclonal-antibodies
NCBI PubMed ID: 26198038Publication DOI: 10.1021/acschembio.5b00502Journal NLM ID: 101282906Publisher: Washington, DC: American Chemical Society
Correspondence: silipo@unina.it
Institutions: Department of Chemical Sciences, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, I-80126, Naples, Italy, Department of Microbiology and Immunology, University of Nevada School of Medicine, Reno, Nevada 89557, United States, Université de Poitiers, Institut de Chimie IC2MP, CNRS-UMR 7285, Équipe Synthèse Organique, 4 rue Michel Brunet, 86073 Poitiers Cedex-9, France, Department of Microbiology and Immunology, University of South Alabama, Mobile, Alabama 36688, United States
Methods: NMR, SDS-PAGE, Western blotting, biological assays, MD simulations, STD NMR, molecular mechanics, SPR, PFG-NMR
- Article ID: 4980
Bayliss M, Donaldson MI, Nepogodiev SA, Pergolizzi G, Scott AE, Harmer NJ, Field RA, Prior JL "Structural characterisation of the capsular polysaccharide expressed by Burkholderia thailandensis strain E555:: wbiI (pKnock-KmR) and assessment of the significance of the 2-O-acetyl group in immune protection" -
Carbohydrate Research 452 (2017) 17-24
Burkholderia pseudomallei and its close relative B. mallei are human pathogens that are classified as Tier 1 bio-threat agents. Both organisms have previously been shown to constitutively produce a capsular polysaccharide (CPS) that is both a virulence determinant and protective antigen. Extraction and purification of CPS for use as a potential vaccine candidate requires containment level 3 laboratories which is expensive and time-consuming. B. thailandensis strain E555 is closely related to B. pseudomallei and B. mallei, but is non-pathogenic to humans and based on immunological cross-reactivity has previously been shown to express a B. pseudomallei-like CPS. In this study, capsular polysaccharide isolated from an O-antigen deficient strain of B. thailandensis E555 was identified by 1H and 13C NMR spectroscopy as -3-)-2-O-acetyl-6-deoxy-β-d-manno-heptopyranose-(-1, and identical to that produced by B. pseudomallei. This was further substantiated by anti-CPS monoclonal antibody binding. In connection with the production of CPS fragments for use in glycoconjugate vaccines, we set out to assess the importance or otherwise of the CPS 2-OAc groups in immune protection. To this end conjugates of the native and de-O-acetylated CPS with the Hc fragment of tetanus toxin (TetHc) were used as vaccines in a mouse model of melioidosis. The level of protection provided by deacetylated CPS was significantly lower than that from native, acetylated CPS. In addition, sera from mice vaccinated with the deacetylated CPS conjugate did not recognise native CPS. This suggests that CPS extracted from B. thailandensis can be used as antigen and that the acetyl group is essential for protection.
capsular polysaccharide, Burkholderia pseudomallei, melioidosis, glycoconjugate vaccine, Burkholderia thailandensis
NCBI PubMed ID: 29024844Publication DOI: 10.1016/j.carres.2017.09.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mbayliss@dstl.gov.uk; rob.field@jic.ac.uk
Institutions: Chemical, Biological and Radiological Division, Defence Science and Technology Laboratory, Porton Down, Salisbury, Wiltshire, SP4 0JQ, UK, Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK, Living Systems Institute, University of Exeter, Stocker Road, Exeter, EX4 4QD, UK, University of Exeter, Stocker Road, Exeter, EX4 4QD, UK, London School of Hygiene and Tropical Medicine, Keppler Street, London, WC1 7HT, UK
Methods: 13C NMR, 1H NMR, SDS-PAGE, sugar analysis, ELISA, acid hydrolysis, Western blotting, biological assays, de-O-acetylation, HPAEC-PAD, antibody binding, conjugation
- 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: 5188
Micoli F, Costantino P, Adamo R "Potential targets for next generation anti-microbial glycoconjugate vaccines" -
FEMS Microbiology Reviews 42(3) (2018) 388-423
Cell surface carbohydrates have been proven optimal targets for vaccine development. Conjugation of polysaccharides to a carrier protein triggers a T-cell dependent immune response to the glycan moiety. Licensed glycoconjugate vaccines are produced by chemical conjugation of capsular polysaccharides to prevent meningitis caused by meningococcus, pneumococcus and Haemophilus influenzae type b. However, other classes of carbohydrates (O-antigens, exopolysaccharides, wall/teichoic acids) represent attractive targets for developing vaccines.Recent analysis from WHO/CHO underpins alarming concern towards antibiotic resistant bacteria, such as the so called ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter spp.) and additional pathogens such as Clostridium difficile and Group A Streptococcus. Fungal infections are also becoming increasingly invasive for immunocompromised patients or hospitalized individuals. Other emergencies could derive from bacteria which spread during environmental calamities (Vibrio cholerae) or with potential as bioterrorism weapons (Burkholderia pseudomallei and mallei, Francisella tularensis). Vaccination could aid reducing the use of broad spectrum antibiotics and provide protection by herd immunity also to individuals who are not vaccinated.This review analyses structural and functional differences of the polysaccharides exposed on the surface of emerging pathogenic bacteria, combined with medical need and technological feasibility of corresponding glycoconjugate vaccines.
carbohydrates, glycoconjugates, vaccines, glycoengineering, antimicrobial resistance
NCBI PubMed ID: 29547971Publication DOI: 10.1093/femsre/fuy011Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: Roberto Adamo
Institutions: GSK Vaccines Institute for Global Health (GVGH), Via Fiorentina 1, 53100 Siena
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2. Compound ID: 1139
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a-Parp-(1-3)-b-D-6dmanHepp-(1-4)-+
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-3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
The structure is contained in the following publication(s):
- Article ID: 345
Pacinelli E, Wang L, Reeves PR "Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB" -
Infection and Immunity 70(6) (2002) 3271-3276
O antigen is part of the lipopolysaccharide present in the outer membrane of gram-negative bacteria and is highly polymorphic. In this study, we obtained sequences of the O-antigen gene clusters for the Yersinia pseudotuberculosis antigens IA, IIA, and IVB. We propose that the IIA gene cluster was derived from the IVB cluster, one of the very few cases in which a parent gene cluster is identified, and that the IA gene cluster could be a hybrid of the IVB and IB gene clusters. All three O antigens contain 6-deoxy-D-mannoheptose, and we identified six genes for the biosynthetic pathway for the precursor of this sugar, GDP-6-deoxy-D-mannoheptose
O-antigen, antigens, gene cluster, Yersinia pseudotuberculosis, relationship, Yersinia
NCBI PubMed ID: 12011023Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing
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3. Compound ID: 1140
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a-Tyvp-(1-3)-a-D-6dmanHep-(1-4)-+
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-3)-a-D-Galp-(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_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
The structure is contained in the following publication(s):
- Article ID: 345
Pacinelli E, Wang L, Reeves PR "Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB" -
Infection and Immunity 70(6) (2002) 3271-3276
O antigen is part of the lipopolysaccharide present in the outer membrane of gram-negative bacteria and is highly polymorphic. In this study, we obtained sequences of the O-antigen gene clusters for the Yersinia pseudotuberculosis antigens IA, IIA, and IVB. We propose that the IIA gene cluster was derived from the IVB cluster, one of the very few cases in which a parent gene cluster is identified, and that the IA gene cluster could be a hybrid of the IVB and IB gene clusters. All three O antigens contain 6-deoxy-D-mannoheptose, and we identified six genes for the biosynthetic pathway for the precursor of this sugar, GDP-6-deoxy-D-mannoheptose
O-antigen, antigens, gene cluster, Yersinia pseudotuberculosis, relationship, Yersinia
NCBI PubMed ID: 12011023Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing
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4. Compound ID: 1141
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a-Abep-(1-3)-b-D-6dmanHep-(1-4)-+
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-3)-a-D-Galp-(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_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
The structure is contained in the following publication(s):
- Article ID: 345
Pacinelli E, Wang L, Reeves PR "Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB" -
Infection and Immunity 70(6) (2002) 3271-3276
O antigen is part of the lipopolysaccharide present in the outer membrane of gram-negative bacteria and is highly polymorphic. In this study, we obtained sequences of the O-antigen gene clusters for the Yersinia pseudotuberculosis antigens IA, IIA, and IVB. We propose that the IIA gene cluster was derived from the IVB cluster, one of the very few cases in which a parent gene cluster is identified, and that the IA gene cluster could be a hybrid of the IVB and IB gene clusters. All three O antigens contain 6-deoxy-D-mannoheptose, and we identified six genes for the biosynthetic pathway for the precursor of this sugar, GDP-6-deoxy-D-mannoheptose
O-antigen, antigens, gene cluster, Yersinia pseudotuberculosis, relationship, Yersinia
NCBI PubMed ID: 12011023Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing
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5. Compound ID: 1227
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a-Parp-(1-3)-b-6dmanHepp-(1-4)-+
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-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
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
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6. Compound ID: 1228
Structure type: fragment of a bigger structure
Compound class: O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_156494,IEDB_190606,IEDB_742246,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
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
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7. Compound ID: 1229
Structure type: fragment of a bigger structure
Compound class: O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_156494,IEDB_190606,IEDB_742246,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
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
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8. Compound ID: 1784
Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142489,SB_86
The structure is contained in the following publication(s):
- Article ID: 560
Feng L, Senchenkova SN, Yang J, Shashkov AS, Tao J, Guo H, Cheng J, Ren Y, Knirel YA, Reeves P, Wang L "Synthesis of the heteropolysaccharide O-antigen of Escherichia coli O52 requires an ABC transporter: Structural and genetic evidences" -
Journal of Bacteriology 186(14) (2004) 4510-4519
The structural and genetic organization of the Escherichia coli O52 O antigen was studied. As identified by sugar and methylation analysis and nuclear magnetic resonance spectroscopy, the O antigen of E. coli O52 has a partially O-acetylated disaccharide repeating unit (O unit) containing D-fucofuranose and 6-deoxy-D-manno-heptopyranose, as well as a minor 6-deoxy-3-O-methylhexose (most likely, 3-O-methylfucose). The O-antigen gene cluster of E. coli O52, which is located between the galF and gnd genes, was found to contain putative genes for the synthesis of the O-antigen constituents, sugar transferase genes, and ABC-2 transporter genes. Further analysis confirmed that O52 employs an ATP-binding cassette (ABC) transporter-dependent pathway for translocation and polymerization of the O unit. This is the first report of an ABC transporter being involved in translocation of a heteropolysaccharide O antigen in E. coli. Genes specific for E. coli O52 were also identified.
genetic, structure, gene, O-antigen, O antigen, Escherichia coli, ABC transporter
NCBI PubMed ID: 15231783Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin Biochip Technology Corporation, Tianjin, China
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, PCR, DNA sequencing, sugar analysis
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9. Compound ID: 1785
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142489,SB_86
The structure is contained in the following publication(s):
- Article ID: 560
Feng L, Senchenkova SN, Yang J, Shashkov AS, Tao J, Guo H, Cheng J, Ren Y, Knirel YA, Reeves P, Wang L "Synthesis of the heteropolysaccharide O-antigen of Escherichia coli O52 requires an ABC transporter: Structural and genetic evidences" -
Journal of Bacteriology 186(14) (2004) 4510-4519
The structural and genetic organization of the Escherichia coli O52 O antigen was studied. As identified by sugar and methylation analysis and nuclear magnetic resonance spectroscopy, the O antigen of E. coli O52 has a partially O-acetylated disaccharide repeating unit (O unit) containing D-fucofuranose and 6-deoxy-D-manno-heptopyranose, as well as a minor 6-deoxy-3-O-methylhexose (most likely, 3-O-methylfucose). The O-antigen gene cluster of E. coli O52, which is located between the galF and gnd genes, was found to contain putative genes for the synthesis of the O-antigen constituents, sugar transferase genes, and ABC-2 transporter genes. Further analysis confirmed that O52 employs an ATP-binding cassette (ABC) transporter-dependent pathway for translocation and polymerization of the O unit. This is the first report of an ABC transporter being involved in translocation of a heteropolysaccharide O antigen in E. coli. Genes specific for E. coli O52 were also identified.
genetic, structure, gene, O-antigen, O antigen, Escherichia coli, ABC transporter
NCBI PubMed ID: 15231783Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin Biochip Technology Corporation, Tianjin, China
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, PCR, DNA sequencing, sugar analysis
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10. Compound ID: 2328
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b-D-Galf-(1-4)-a-L-Rhap-(1-3)-+
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-4)-D-gro-b-D-manHepp-(1-3)-b-D-6dmanHepp2Ac-(1-4)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136095,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 794
Czaja J, Jachymek W, Niedziela T, Lugowski C, Aldova E, Kenne L "Structural studies of the O-specific polysaccharides from Plesiomonas shigelloides strain CNCTC113/92" -
European Journal of Biochemistry 267 (2000) 1672-1679
The structure of the O-specific side chain of the lipopolysaccharide (LPS) of Plesiomonas shigelloides, strain CNCTC113/92 has been investigated by NMR spectroscopy, matrix-assisted laser desorption/ionization time of flight mass spectrometry and sugar and methylation analysis. It was concluded that the polysaccharide is composed of a hexasaccharide repeating unit with the following structure: in which D-β-D-Hepp is Dglycero-β-Dmanno-heptopyranose and 6d-β-D-Hep is 6-deoxy-β-Dmanno-heptopyranose. This structure represents a novel hexasaccharide repeating unit of bacterial O-antigen that is characteristic and unique to the Plesiomonas shigelloides strain. Using the high-resolution magic angle spinning technique, 1H NMR spectra were also obtained for the O-polysaccharide components of isolated LPS and in their original form directly on the surface of bacterial cells.
NMR, lipopolysaccharides, structure, strain, structural, polysaccharide, bacteria, O-specific, O-specific polysaccharide, polysaccharides, surface, structural studies, O-specific polysaccharides, native, high-resolution, magic angle, Plesiomonas, Plesiomonas shigelloides
NCBI PubMed ID: 10712598Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Lennart.Kenne@kemi.slu.se
Institutions: L. Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland, Swedish University of Agricultural Sciences, Uppsala, Sweden, National Institute of Public Health, Prague, Czech Republic
Methods: NMR-2D, NMR, sugar analysis
- 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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11. Compound ID: 2987
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b-D-Galp-(1-4)-+ L-gro-a-D-manHepp-(1-7)-+ b-D-Galp-(1-4)-+
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b-D-Galf-(1-4)-a-L-Rhap-(1-3)-D-gro-b-D-manHepp-(1-3)-b-D-6dmanHepp2Ac-(1-4)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-4)-b-D-Glcp-(1-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
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b-D-Glcp-(1-2)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135813,IEDB_135849,IEDB_136044,IEDB_136095,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1050
Niedziela T, Lukasiewicz J, Jachymek W, Dzieciatkowska M, Lugowski C, Kenne L "Core oligosaccharides of Plesiomonas shigelloides O54:H2(strain CNCTC113/92). Structural and serological analysis of the lipopolysaccharide core region, the O-antigen biological repeating unit and the linkage between them" -
Journal of Biological Chemistry 277(14) (2002) 11653-11663
The structure of the core oligosaccharide moiety of the lipopolysaccharide (LPS) of Plesiomonas shigelloides O54 (strain CNCTC113/92) has been investigated by 1H and 13C NMR, FAB-MS/MS, MALDI-TOF MS, monosaccharide and methylation analysis and immunological methods. It was concluded that the main core oligosaccharide of this strain is composed of a decasaccharide with the presented structure in which L-a- D-Hepp is L-glycero-a-D-manno-heptopyranose. The nonasaccharide variant of the core oligosaccharide (~10%), devoid of b-D-Glcp substituting the a-D-GlcpN at C-6, was also identified. The core oligosaccharide substituted at C-4 of the outer core b-D-Glcp residue with the single O-polysaccharide repeating unit was also isolated yielding a hexadecasaccharide structure. The determination of the monosaccharides involved in the linkage between the O-specific polysaccharide part and the core, as well as the presence of 3-substituted D-b-D-Hepp instead of 3,4-disubstituted D-b-D-Hepp in the repeating unit, revealed the structure of the biological repeating unit of the O-antigen. The core oligosaccharides are not substituted by phosphate residues and represent novel core type of bacterial LPS that is characteristic for the Plesiomonas shigelloides serotype O54. Serological screening of 69 different O-serotypes of P. shigelloides suggests that epitopes similar to the core oligosaccharide of serotype O54 (strain CNCTC113/92) might also be present in the core region of the serotypes O24 (strain CNCTC92/89), O37 (strain CNCTC39/89) and O96 (strain CNCTC5133) LPS
Lipopolysaccharide, NMR, LPS, oligosaccharide, structure, core, chemistry, Bacterial, strain, structural, polysaccharide, serotype, methylation analysis, O-antigen, repeating unit, analysis, O antigen, determination, epitope, phosphate, Oligosaccharides, type, core oligosaccharide, immunological, lipopolysaccharide core, epitopes, O polysaccharide, O-specific, O-specific polysaccharide, serological, biological, linkage, core region, region, methylation, method, MALDI-TOF, 13C NMR, Serotypes, methods, variant, MS, monosaccharide, O-serotype, biological repeating unit, MALDI-TOF MS, Plesiomonas, Plesiomonas shigelloides, monosaccharides
NCBI PubMed ID: 11796731Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Lennart.Kenne@kemi.slu.se
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala SE-75007, L. Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw PL-53114, Poland
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, FAB-MS, NMR, MALDI-TOF MS, serological methods
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12. Compound ID: 4609
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a-Parp-(1-3)-b-D-6dmanHepp-(1-4)-+
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-3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
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: 1824
Komandrova NA, Gorshkova RP, Isakov VV, Ovodov YS "Structure of the O-specific polysaccharide isolated from lipopolysaccharide of Yersinia pseudotuberculosis serovar 1A" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 10(2) (1984) 232-237
An O-specific polysaccharide from the lipopolysaccharide Yersinia pseudotuberculosis 1A serovar has been isolated and characterized. This compound was shown to contain residues of paratose, 6-deoxy-D-manno-heptose, D-galactose and 2-amino-2-deoxy-D-glucose in equimolar ratios. Using methylation studies, partial acid hydrolysis and 13C NMR spectroscopy, the following structure was proposed for the repeating unit of the O-specific polysaccharide: (Formula: see text).
NCBI PubMed ID: 6207836Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Sciences Center, Academy of Sciences of the USSR, Vladivostok
Methods: 13C NMR
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13. Compound ID: 4650
Structure type: homopolymer
Compound class: O-polysaccharide, O-antigen
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: 2228
Knirel YA, Paramonov NA, Shashkov AS, Kochetkov NK, Yarullin RG, Farber SM, Efremenko VI "Structure of the polysaccharide chains of Pseudomonas pseudomallei lipopolysaccharides" -
Carbohydrate Research 233 (1992) 185-193
The pathogenic bacterium Pseudomonas pseudomallei strain 57576 produces two partially O-acetylated O-antigenic polysaccharides (PS-I and PS-II). Methylation analysis and 1H and 13C NMR spectroscopy, including NOE experiments, showed PS-I to have the structure [formula: see text] and PS-II to have the structure [formula: see text] where 6dmanHep is the unusual higher sugar 6-deoxy-D-manno-heptose. PS-II is produced also by P. pseudomallei strains 100 and 110, and PS-I and O-deacetylated PS-II by strain 97.
Lipopolysaccharide, O-antigen, NMR spectroscopy, O-polysaccharide, Pseudomonas pseudomallei, 6-deoxy-D-manno-heptose
NCBI PubMed ID: 1280183Publication DOI: 10.1016/S0008-6215(00)90930-3Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Antiplague Research Institute, Health Ministry, Volgograd, Russia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, paper chromatography, de-O-acetylation
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14. Compound ID: 5849
Structure type: oligomer
Trivial name: O-antigen side chain of LPS
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2575
Samuelsson K, Lindberg B, Brubaker RR "Structure of O-specific side chains of lipopolysaccharides from Yersinia pseudotuberculosis" -
Journal of Bacteriology 117 (1974) 1010-1016
Journal NLM ID: 2985120RPublisher: American Society for Microbiology
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15. Compound ID: 6964
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b-D-Galf-(1-4)-a-L-Rhap-(1-3)-+ b-D-Galp-(1-4)-+ L-gro-a-D-manHepp-(1-7)-+ b-D-Galp-(1-4)-+ a-Kdop-(2-4)-+
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{{{-D-gro-b-D-manHepp-(1-3)-b-D-6dmanHepp2Ac-(1-4)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-4)-}}}b-D-Glcp-(1-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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b-D-Glcp-(1-2)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135813,IEDB_135849,IEDB_136044,IEDB_136095,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3180
Lukasiewicz J, Niedziela T, Jachymek W, Kenne L, Lugowski C "Structure of the lipid A-inner core region and biological activity of Plesiomonas shigelloides O54 (strain CNCTC 113/92) lipopolysaccharide" -
Glycobiology 16(6) (2006) 538-550
Plesiomonas shigelloides is a Gram-negative rod, associated with episodes of intestinal infections and outbreaks of diarrhoea in humans. The extraintestinal infections caused by this bacterium, e.g., endopthalmitis, meningitidis, bacteraemia and septicaemia, usually have gastrointestinal origin and serious course. The lipopolysaccharide (LPS, endotoxin) as virulence factor is important in enteropathogenicity of this bacterium. Lipopolysaccharides of P. shigelloides and especially their lipid A part, i.e. the immunomodulatory centre of LPS, have not been extensively investigated. The structure of P. shigelloides O54 lipid A was determined by chemical analysis combined with MALDI-TOF mass spectrometry and the intact Kdo-containing core region was investigated by NMR spectroscopy on deacylated LPS. Products from alkaline deacylation of LPS, containing 4-substituted uronic acids are usually very complex and difficult to separate. Since Kdo residues as sialic acids form complexes with serotonin, we used immobilised serotonin for one-step isolation of oligosaccharide containing the intact Kdo region from the reaction mixture by affinity chromatography. The major form of lipid A was built of β-D-GlcpN4PPEtn-(1→6)-α-D-GlcpN1P disaccharide substituted with 14:0(3-OH), 12:0(3-OH), 14:0(3-O-14:0) and 12:0(3-O-12:0) acyl groups at N-2, O-3, N-2' and O-3', respectively. This is a novel structure among known lipid A molecules. Analysis of intact Kdo-lipid A region, lipid A and its linkage with the core oligosaccharide completes the structural investigation of P. shigelloides O54 LPS, resolving the entire molecule. Biological activities and observed discrepancy between in vitro and in vivo activity of P. shigelloides and Escherichia coli LPS are discussed.
Lipopolysaccharide, lipid A, NMR spectroscopy, MALDI-TOF mass spectrometry, Plesiomonas shigelloides
NCBI PubMed ID: 16490765Publication DOI: 10.1093/glycob/cwj094Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: czaja@iitd.pan.wroc.pl
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Immunochemistry, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, R. Wroclaw, Poland
Methods: GC-MS, NMR, MALDI-TOF MS, de-N-O-acylation
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