The conformational properties of methyl α-(2,8)-di/trisialosides and their N-acyl analogues: Implications for anti-Neisseria meningitidis B vaccine design

Biochemistry

Volumn 47, Issue 47, 2008, Pages 12493-12514

  Yongye, Austin B ^a   Gonzalez Outeiriño, Jorge ^a   Glushka, John ^a   Schultheis, Verena ^b   Woods, Robert J ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ANTIBODIES; CHEMICAL MODIFICATION; DYNAMICS; MOLECULAR DYNAMICS; MONOCLONAL ANTIBODIES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE SPACE METHODS; POLYSACCHARIDES; QUANTUM CHEMISTRY;

ACYL GROUPS; ANTIBODY RESPONSES; BAYESIAN; CAPSULAR POLYSACCHARIDES; CHEMICAL GROUPS; CONFORMATIONAL DISTRIBUTIONS; CONFORMATIONAL EPITOPES; CONFORMATIONAL PROPERTIES; FORCE FIELDS; IMMUNOGENICITY; NEISSERIA MENINGITIDIS; NMR SPECTROSCOPIES; POLYSIALIC ACIDS; PROPIONYL; REPLICA EXCHANGES; STATISTICAL ANALYSIS; STRUCTURAL DIFFERENCES; TORSION ANGLES; VACCINE DESIGNS;

CHEMICAL PROPERTIES;

BACTERIAL POLYSACCHARIDE; BACTERIAL VACCINE; DISACCHARIDE; EPITOPE; METHYL ALPHA (2,8) DISIALOSIDE; METHYL ALPHA (2,8) TRISIALOSIDE; MONOCLONAL ANTIBODY; N ACETYL ALPHA (2,8) TRISIALOSIDE; N BUTANOYL ALPHA (2,8) TRISIALOSIDE; N GLYCOLYL ALPHA (2,8) TRISIALOSIDE; N PROPIONYL ALPHA (2,8) TRISIALOSIDE; N PROPYL ALPHA (2,8) TRISIALOSIDE; NEISSERIA MENINGITIDIS B VACCINE; O ANTIGEN; POLYSIALIC ACID; TRISACCHARIDE; UNCLASSIFIED DRUG;

ANTIBODY RESPONSE; ARTICLE; BAYES THEOREM; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; CROSS REACTION; DRUG DESIGN; DRUG STRUCTURE; IMMUNOGENICITY; MOLECULAR DYNAMICS; NEISSERIA MENINGITIDIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; SIMULATION; STRUCTURE ANALYSIS;

ANTIBODIES, BACTERIAL; BACTERIAL CAPSULES; BACTERIAL VACCINES; CARBOHYDRATE CONFORMATION; CROSS REACTIONS; DRUG DESIGN; HAPTENS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NEISSERIA MENINGITIDIS, SEROGROUP B; SIALIC ACIDS;

NEISSERIA MENINGITIDIS;

EID: 56749148321     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi800431c     Document Type: Article

References (52)

1. Ferreiros, C. M., Gomez, J. A., and Criado, M. T. (1998) Prevention of meningococcal disease: present and future. Rev. Med. Microbiol. 9, 29-37.
2. Tikhomirov, E., Santamaria, M., and Esteves, K. (1997) Meningococcal disease: public health burden and control. World Health Stat. Q. 50, 170-177.
3. Tsang, R. S. W., and Zollinger, W. D. (2005) Serological specificities of murine hybridoma monoclonal antibodies against Neisseria meningitidis serogroups B, C, Y and W135 and evaluation of their usefulness as serogrouping reagents by indirect whole-cell enzyme-linked immunosorbent assay. Clin. Diagn. Lab. Immunol. 12, 152-156.
4. Bardotti, A., Averani, G., Berti, F., Berti, S., Galli, C., Giannini, S., Fabbri, B., Proietti, D., Ravenscroft, N., and Ricci, S. (2005) Size determination of bacterial capsular oligosaccharides used to prepare conjugate vaccines against Neisseria meningitidis groups Y and W135. Vaccine 23, 1887-1899.
5. Bhattacharjee, A. K., Jennings, H. J., Kenny, C. P., Martin, A., and Smith, I. C. P. (1976) Structural determination of polysaccharide antigens of Neisseria meningitidis serogroup Y, serogroup W-135, and serogroup BO. Can. J. Biochem. 54, 1-8.
6. Bhattacharjee, A. K., Jennings, H. J., Kenny, C. P., Martin, A., and Smith, I. C. P. (1975) Structural determination of sialic acid polysaccharide antigens of Neisseria meningitidis serogroup B and serogroup C with C-13 nuclear magnetic resonance. J. Biol. Chem. 250, 1926-1932.
7. Bundle, D. R., Smith, I. C. P., and Jennings, H. J. (1974) Determination of the structure and conformation of bacterial polysaccharides by carbon 13 nuclear magnetic resonance. Studies on group-specific antigens of Neisseria meningitidis serogroups A and X. J. Biol. Chem. 249, 2275-2281.
8. NOV. J. Exp. Med. 168, 699-711.
9. Brisson, J. R., Baumann, H., Imberty, A., Perez, S., and Jennings, H. J. (1992) Helical epitope of the group B meningococcal α-(2-8)-linked sialic acid polysaccharide. Biochemistry 31, 4996-5004.
10. Jennings, H. J., Roy, R., and Michon, F. (1985) Determinant specificities of the group B and group C polysaccharides of Neisseria meningitidis. J. Immunol. 134, 2651-2657.
11. Baumann, H., Brisson, J. R., Michon, F., Pon, R., and Jennings, H. J. (1993) Comparison of the conformation of the epitope of α-(2- 8) polysialic acid with its reduced and N-acyl derivatives. Biochemistry 32, 4007-4013.
12. Weintraub, A. (2003) Immunology of bacterial polysaccharide antigens. Carbohydr. Res. 338, 2539-2547.
13. Finne, J., Leinonen, M., and Makela, P. H. (1983) Antigenic similarities between brain components and bacteria causing meningitis. Implications for vaccine development and pathogenesis. Lancet 2, 355-357.
14. Granoff, D. M., Bartoloni, A., Ricci, S., Gallo, E., Rosa, D., Ravenscroft, N., Guarnieri, V., Seid, R. C., Shan, A., Usinger, W. R., Tan, S., McHugh, Y. E., and Moe, G. R. (1998) Bactericidal monoclonal antibodies that define unique meningococcal B polysaccharide epitopes that do not cross-react with human polysialic aicd. J. Immunol. 160, 5028-5036.
15. Devi, S. J. N., Robbins, J. B., and Schneerson, R. (1991) Antibodies to poly[(2-8)-α-N-acetylneuraminic acid] and poly[(2-9)-α-N- acetylneuraminc acid] are elicited by immunization of mice with Escherichia coli K92 conjugates: Potential vaccines for groups B and C meningococci and E. coli K1. Proc. Natl. Acad. Sci. U.S.A. 88, 7175-7179.
16. Lifely, M. R., Gilbert, A. S., and Moreno, C. (1981) Sialic acid polysaccharide antigens of Neisseria meningitidis and Escherichia coli. Esterification between adjacent residues. Carbohydr. Res. 94, 193-203.
17. Azurmendi, H. F., Vionnet, J., Wrightson, L., Trinh, L. B., Shiloach, J., and Freedberg, D. I. (2007) Extracellular structure of polysialic acid explored by on cell solution NMR. Proc. Natl. Acad. Sci. U.S.A. 104, 11557-11561.
18. Evans, S. V., Sigurskjold, B. W., Jennings, H. J., Brisson, J. R., To, R., Tse, W. C., Altman, E., Frosch, M., Weisgerber, C., Kratzin, H. D., Klebert, S., Vaesen, M., Bittersuermann, D., Rose, D. R., Young, N. M., and Bundle, D. R. (1995) Evidence for the extended helical nature of polysaccharide epitopes. The 2.8Å resolution structure and thermodynamics of ligand binding of an antigen binding fragment specific for α-(2- 8)-polysialic acid. Biochemistry 34, 6737-6744.
19. Jennings, H. J., Roy, R., and Gamian, A. (1986) Induction of meningococcal group B polysaccharide-specific IgG antibodies in mice by using an N-propionylated B polysaccharide-tetanus toxoid conjugate vaccine. J. Immunol. 137, 1708-1713.
20. Lifely, M. R., and Esdaile, J. (1991) Specificity of the immune response to the group B polysaccharide of Neisseria meningitidis. Immunology 74, 490-496.
21. Pon, R. A., Khieu, N. H., Yang, Q. L., Brisson, J. R., and Jennings, H. J. (2002) Serological and conformational properties of E. coli K92 capsular polysaccharide and its N-propionylated derivative both illustrate that induced antibody does not recognize extended epitopes of polysialic acid: Implications for a comprehensive conjugate vaccine against groups B and C N. meningitidis. Can. J. Chem. 80, 1055-1063.
22. Pon, R. A., Lussier, M., Yang, Q. L., and Jennings, H. J. (1997) N-propionylated group B meningococcal polysaccharide mimics a unique bactericidal capsular epitope in group B Neisseria meningitidis. J. Exp. Med. 185, 1929-1938.
23. Pon, R. A., Biggs, N. J., and Jennings, H. J. (2007) Polysialic acid bioengineering of neuronal cells by N-acyl sialic acid precursor treatment. Glycobiology 17, 249-260.
24. Lifely, M. R., Lindon, J. C., Williams, J. M., and Moreno, C. (1985) Structural and conformational features of the Escherichia coli K92 capsular polysaccharide. Carbohydr. Res. 143, 191-205.
25. Henderson, T. J., Venable, R. M., and Egan, W. (2003) Conformational flexibility of the group B meningococcal polysaccharide in solution. J. Am. Chem. Soc. 125, 2930-2939.
26. Venable, R. M., Bizik, F., Henderson, T. J., and Egan, W. (1997) Molecular dynamics simulations of an α-(2-> 8)-linked sialic acid tetramer in vacuum and solvent. J. Mol. Struct. (THEOCHEM) 395, 375-388.
27. Cumming, D. A., and Carver, J. P. (1987) Virtual and Solution Conformations of Oligosaccharides. Biochemistry 26, 6664-6676.
28. Gonzalez-Outeirino, J., Kadirvelraj, R., and Woods, R. J. (2005) Structural elucidation of type III group B Streptococcus capsular polysaccharide using molecular dynamics simulations: the role of sialic acid. Carbohydr. Res. 340, 1007-1018.
29. Vasudevan, S. V., and Balaji, P. V. (2002) Molecular dynamics of alpha2-8 linked disialoside: Conformational analysis and implications for binding to proteins. Biopolymers 63, 168-180.
30. Kirschner, K. N., and Woods, R. J. (2001) Solvent interactions determine carbohydrate conformation. Proc. Natl. Acad. Sci. U.S.A. 98, 10541-10545.
31. Gonzalez-Outeirino, J., Kirschner, K. N., Thobhani, S., and Woods, R. J. (2006) Reconciling solvent effects on rotamer populations in carbohydrates - A joint MD and NMR analysis. Can. J. Chem. 84, 569-579.
32. Kirschner, K. N., Yongye, A. B., Gonzalez-Outeirino, J., Tschampel, S. M., Daniels, C. R., Foley, B. L., and Woods, R. J. (2008) GLYCAM06: A Generalizable Biomolecular Force Field. Carbohydrates. J. Comput. Chem. 29, 622-655.
33. Yongye, A. B., Foley, B. L., and Woods, R. J. (2008) On achieving experimental accuracy from molecular dynamics simulations of flexible molecules: aqueous glycerol. J. Phys. Chem. A 112, 2634-2639.
34. Case, D. A., Darden, T. A., Cheatham, T. E., III, Simmerling, C. L., Wang, J., Duke, R. E., Lou, R., Merz, K. M., Wang, B., Pearlman, D. A., Crowley, M., Brozell, S., Tsui, V., Gohlke, H., Mongan, J., Hornak, V., Cui, G., Beroza, P., Schafmeister, P., Caldwell, J. W., Ross, W. S., and Kollman, P. A. (2004) AMBER 8, University of California, San Francisco, CA.
35. Jorgensen, W. L., and Swenson, C. J. (1985) Optimised intermolecular potential functions for amides and peptides. Structure and properties of liquid amides. J. Am. Chem. Soc. 107, 569-578.
36. Darden, T., York, D., and Pederson, L. (1993) Particle mesh Ewald: A N.log(N) method for Ewald sums in large systems. J. Chem. Phys. 98, 10089-10092.
37. van Gunsteren, W. F., and Berendsen, H. J. C. (1977) Algorithms for macromolecular dynamics and constraint dynamics. Mol. Phys. 34, 1311-1327.
38. Okur, A., Wickstrom, L., Layten, M., Geney, R., Song, K., Hornak, V., and Simmerling, C. (2006) Improved efficiency of replica exchange simulations through use of a hybrid explicit/implicit solvation model. J. Chem. Theory Comput. 2, 420-433.
39. Rathore, N., Chopra, M. J., and de.Pablo, J. (2005) Optimal allocation of replicas in parallel tempering simulations. J. Chem. Phys. 122, 024111.
40. Schultheis, V., Hirschberger, T., Carstens, H., and Tavan, P. (2005) Extracting Markov models of peptide conformational dynamics from simulation data. J. Chem. Theory Comput. 1, 515-526.
41. Kloppenburg, M., and Tavan, P. (1997) Deterministic annealing for density estimation by multivariate normal mixtures. Phys. Rev. E 55, R2089-R2092.
42. James, T. L., and Leu, H. E. (1999) CORMA, University of California, San Francisco.
43. Thrippleton, M. J., and Keeler, J. (2003) Elimination of zero-quantum interference in two-dimensional NMR spectra. Angew. Chem., Int. Ed. 42, 3938-3941.
44. Delaglio, F., Grzesiek, S., Vuister, G. W., Zhu, G., Pfeifer, J., and Bax, A. (1995) Nmrpipe - A Multidimensional Spectral Processing System Based On Unix Pipes. J. Biomol. NMR 6, 277-293.
45. NMRView, NMRView Software; One Moon, Scientific, Inc.
46. Michon, F., Brisson, J. R., and Jennings, H. J. (1987) Conformational differences between linear α-(2-8)-linked homosialooligosaccharides and the epitope of the group B meningococcal polysaccharide. Biochemistry 26, 8399-8405.
47. Haasnoot, C. A. G., Deleeuw, F., and Altona, C. (1981) Relationship between Proton-Proton NMR Coupling-Constants and Substituent Electronegativities.I. An empirical generalization of the Karplus Equation. Tetrahedron 36, 2783-2792.
48. Kooijman, H., Kroonbatenburg, L. M. J., Kroon, J., Breg, J. N., and Deboer, J. L. (1990) Structure of α-D-N-acetyl-1-O-methyl- neuraminic acid methyl ester. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 46, 407-410.
49. Poppe, L., Stuike-Prill, S., Meyer, B., and van Halbeek, H. (1992) The solution conformation of sialyl-α-(2,6)-lactose studied by modern NMR techniques and Monte Carlo simulation. J. Biomol. NMR 2, 109-136.
50. 1H-NMR spectroscopy in combination with energy calculations by hard-sphere exo- anomeric and molecular mechanics force-field with hydrogen-bonding potential. Eur. J. Biochem. 178, 727-739.
51. Woods, R. J., Pathiaseril, A., Wormald, M. R., Edge, C. J., and Dwek, R. A. (1998) The high degree of internal flexibility observed for an oligomannose oligosaccharide does not alter the overall topology of the molecule. Eur. J. Biochem. 158, 372-386.
52. Sugeta, H., and Miyazawa, T. (1967) General method for calculating helical parameters of polymer chains from bond lengths, bond angles and internal rotation angles. Biopolymers 5, 673-679.