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Pure Appl. Chem., 1984, Vol. 56, No. 7, pp. 893-905

http://dx.doi.org/10.1351/pac198456070893

Structure, conformation and immunology of sialic acid-containing polysaccharides of human pathogenic bacteria

H. J. Jennings, Ewa Katzenellenbogen, Czeslaw Lugowski, F. Michon, R. Roy and D. L. Kasper

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  • Johal A. R., Jarrell H. C., Letts J. A., Khieu N. H., Landry R. C., Jachymek W., Yang Q., Jennings H. J., Brisson J.-R., Evans S. V.: The antigen-binding site of an N-propionylated polysialic acid-specific antibody protective against group B meningococci is consistent with extended epitopes. Glycobiology 2013, 23, 946. <http://dx.doi.org/10.1093/glycob/cwt031>
  • Guttormsen H.-K., Paoletti L. C., Mansfield K. G., Jachymek W., Jennings H. J., Kasper D. L.: Rational chemical design of the carbohydrate in a glycoconjugate vaccine enhances IgM-to-IgG switching. Proceedings of the National Academy of Sciences 2008, 105, 5903. <http://dx.doi.org/10.1073/pnas.0710799105>
  • Jokilammi Anne, Ollikka Pauli, Korja Miikka, Jakobsson Elina, Loimaranta Vuokko, Haataja Sauli, Hirvonen Harri, Finne Jukka: Construction of antibody mimics from a noncatalytic enzyme–detection of polysialic acid. J  Immunol Methods 2004, 295, 149. <http://dx.doi.org/10.1016/j.jim.2004.10.006>
  • Zou Wei, Li JianJun, Larocque Suzon, Jennings Harold J: Construction of multivalent sialyl Lex from the type Ia group B Streptococcus capsular polysaccharide. Carbohydrates Research 2001, 332, 249. <http://dx.doi.org/10.1016/S0008-6215(01)00098-2>
  • Bystricky Slavomir, Pavliak Viliam, Szu Shousun C.: Characterization of colominic acid by circular dichroism and viscosity analysis. biophys chem 1997, 63, 147. <http://dx.doi.org/10.1016/S0301-4622(96)02242-9>
  • Zou Wei, Jennings Harold J.: Mimics of the structural elements of type III group B Streptococcus capsular polysaccharide. Part III: two repeating units (octasaccharide) with (S)-1-carboxyethyl groups replacing sialic acids. Biorg Med Chem Lett 1997, 7, 647. <http://dx.doi.org/10.1016/S0960-894X(97)00077-2>
  • Jennings Harold J.: N-Propionylated group B meningococcal polysaccharide glycoconjugate vaccine against group B meningococcal meningitis. International Journal of Infectious Diseases 1997, 1, 158. <http://dx.doi.org/10.1016/S1201-9712(97)90080-1>
  • Zou Wei, Brisson Jean-Robert, Yang Qing-Ling, van der Zwan Mark, Jennings Harold J.: Synthesis and NMR assignment of two repeating units (decasaccharide) of the type III group B Streptococcus capsular polysaccharide and its 13C-labeled and N-propionyl substituted sialic acid analogues. Carbohydrates Research 1996, 295, 209. <http://dx.doi.org/10.1016/S0008-6215(96)90144-5>
  • Jennings Harold J., Zou Wei: Mimics of the Structural Elements of Type III Group B Streptococcus Capsular Polysaccharide. Part I: Synthesis of a Carboxylate-Containing Pentasaccharide. J Carbohydr Chem 1996, 15, 257. <http://dx.doi.org/10.1080/07328309608005652>
  • Zou Wei, Jennings Harold J.: Mimics of the Structural Elements of Type III Group B Streptococcus Capsular Polysaccharide. Part II: Synthesis of a Carboxylate-Containing Hexasaccharide with a Short Spacer. J Carbohydr Chem 1996, 15, 279. <http://dx.doi.org/10.1080/07328309608005653>
  • Zou Wei, Jennings Harold J.: Chemical-Enzymatic Synthesis of A Branched Hexasaccharide Fragment of Type Ia Group B Streptococcus Capsular Polysaccharide. J Carbohydr Chem 1996, 15, 925. <http://dx.doi.org/10.1080/07328309608005699>
  • Devi Sarvamangala J.N., Karpas Arthur B., Frasch Carl E.: Binding diversity of monoclonal antibodies to α(2 → 8) polysialic acid conjugated to outer membrane vesicle via adipic acid dihydrazide. FEMS Immunol Med Microbiol 1996, 14, 211. <http://dx.doi.org/10.1111/j.1574-695X.1996.tb00289.x>
  • Kogan Grigorij, Brisson Jean-Robert, Kasper Dennis L., von Hunolstein Christina, Orefici Graziella, Jennings Harold J.: Structural elucidation of the novel type VII group B Streptococcus capsular polysaccharide by high resolution NMR spectroscopy. Carbohydrates Research 1995, 277, 1. <http://dx.doi.org/10.1016/0008-6215(95)00195-Y>
  • Kogan Grigorij, Uhrín Dušan, Brisson Jean-Robert, Paoletti Lawrence C., Kasper Dennis L., Hunolstein Christina von, Orefici Graziella, Jennings Harold J.: Structure of the Type VI Group B Streptococcus Capsular Polysaccharide Determined by High Resolution NMR Spectroscopy. J Carbohydr Chem 1994, 13, 1071. <http://dx.doi.org/10.1080/07328309408011849>
  • Matthews Ian, Petrak Karel: The preparation and characterization of a twin-tailed, lipid-linked polysialic acid. Biopolymers (Biospectroscopy) 1993, 33, 453. <http://dx.doi.org/10.1002/bip.360330311>
  • KRAUSS Jurgen Hinrich, HIMMELSPACH Karl, REUTER Gerd, SCHAUER Roland, MAYER Hubert: Structural analysis of a novel sialic-acid-containing trisaccharide from Rhodobacter capsulatus 37b4 lipopolysaccharide. Eur J Biochem 1992, 204, 217. <http://dx.doi.org/10.1111/j.1432-1033.1992.tb16627.x>
  • Sabesan Subramaniam, Bock Klaus, Paulson James C.: Conformational analysis of sialyloligosaccharides. Carbohydrates Research 1991, 218, 27. <http://dx.doi.org/10.1016/0008-6215(91)84084-R>
  • Crescenzi V., Dentini M., Coviello T.: Solution and gelling properties of polysaccharide polyelectrolytes. biophys chem 1991, 41, 61. <http://dx.doi.org/10.1016/0301-4622(91)87210-V>
  • Häyrinen Jukka, Bitter-Suermann Dieter, Flnne Jukka: Interaction of meningococcal group B monoclonal antibody and its Fab fragment with α2-8-linked sialic acid polymers: Requirement of a long oligosaccharide segment for binding. Molec Immunol 1989, 26, 523. <http://dx.doi.org/10.1016/0161-5890(89)90003-5>
  • Häyrinen J., Pelkonen S., Finne J.: Structural similarity of the type-specific group B streptococcal polysaccharides and the carbohydrate units of tissue glycoproteins: evaluation of possible cross-reactivity. Vaccine 1989, 7, 217. <http://dx.doi.org/10.1016/0264-410X(89)90232-6>
  • Orefici G., Recchia S., Galante L.: Possible virulence marker forStreptococcus agalactiae (Lancefield group B). Eur J Clin Microbiol Infect Dis 1988, 7, 302. <http://dx.doi.org/10.1007/BF01963108>
  • Bitter-Suermann Dieter, Roth Jürgen: Monoclonal antibodies to polysialic acid reveal epitope sharing between invasive pathogenic bacteria, differentiating cells and tumor cells. IR 1987, 6, 225. <http://dx.doi.org/10.1007/BF02935517>
  • Birnbaum George I., Roy René, Brisson Jean-Robert, Jennings Harold J.: Conformations of Ammonium 3-Deoxy-D-manno-2-octulosonate (KDO) and Methyl α- and β-Ketopyranosides of KDO: X-Ray Structure and 1H NMR Analyses. J Carbohydr Chem 1987, 6, 17. <http://dx.doi.org/10.1080/07328308708058858>
  • Gross Wolfgang L., Levy Nancy J., Kasper Dennis L.: Human lymphocytes response to bacterial products. Clinical Immunology Newsletter 1986, 7, 23. <http://dx.doi.org/10.1016/S0197-1859(86)80008-5>
  • Schauer Roland: Sialic acids and their role as biological masks. Trends Biochem Sci 1985, 10, 357. <http://dx.doi.org/10.1016/0968-0004(85)90112-4>