Erratum: Recent mechanistic insights on glycoconjugate vaccines and future perspectives (ACS Chemical Biology (2013) 8 (1653-1663) DOI: 10.1021/cb400423g);Recent mechanistic insights on glycoconjugate vaccines and future perspectives

ACS Chemical Biology

Volumn 8, Issue 8, 2013, Pages 1653-1663

  Berti, Francesco ^a   Adamo, Roberto ^a  

^a NOVARTIS VACCINES AND DIAGNOSTICS   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM POTASSIUM SULFATE; BACTERIAL VACCINE; CARRIER PROTEIN; CHITIN; CHITOSAN; EPITOPE; GLUCAN; GLYCAN; GLYCOCONJUGATE; IMMUNOLOGICAL ADJUVANT; INULIN; LIPOSOME; MANNAN; MIFAMURTIDE; POLYSACCHARIDE;

ADAPTIVE IMMUNITY; BACTERIAL INFECTION; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CD4+ T LYMPHOCYTE; CHEMICAL STRUCTURE; CONJUGATION; COVALENT BOND; HAEMOPHILUS INFLUENZAE TYPE B; IMMUNE RESPONSE; IMMUNOGENICITY; NEISSERIA MENINGITIDIS; NONHUMAN; PRIORITY JOURNAL; PROTEOGLYCAN SYNTHESIS; REVIEW; STREPTOCOCCUS PNEUMONIAE; T LYMPHOCYTE ACTIVATION; VACCINATION;

HAEMOPHILUS INFLUENZAE SEROTYPE B; NEISSERIA MENINGITIDIS; STREPTOCOCCUS PNEUMONIAE;

ANTIGENS, BACTERIAL; COMMUNICABLE DISEASES; DRUG DESIGN; GLYCOCONJUGATES; HUMANS; LYMPHOCYTE ACTIVATION; MODELS, BIOLOGICAL; T-LYMPHOCYTES; VACCINATION; VACCINES;

EID: 84882791693     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb500822h     Document Type: Erratum

References (105)

1. Donati, C. and Rappuoli, R. (2013) Reverse vaccinology in the 21st century: improvements over the original design Ann. N.Y. Acad. Sci., Mar. 25 10.1111/nyas.12046
2. Kelly, D. F., Pollard, A. J., and Moxon, E. R. (2005) Immunological memory. The role of B cells in long-term protection against invasive bacterial pathogens J. Am. Med. Assoc. 294 (23) 3019-3023
3. Avery, O. T. and Goebel, W. F. (1931) Chemo-immunological studies on conjugated carbohydrate-proteins J. Exp. Med. 54, 437-447
4. Heath, P. T. (1998) Haemophilus influenzae type b conjugate vaccines: A review of efficacy data Pediatr. Infect. Dis. J. 17, S117-S122
5. Campbell, H., Andrews, N., Borrow, R., Trotter, C., and Miller, E. (2010) Updated postlicensure surveillance of the meningococcal C conjugate vaccine in England and Wales: Effectiveness, validation of serological correlates of protection, and modeling predictions of the duration of herd immunity Clin. Vaccine Immunol. 17, 840-847
6. Avci, F. Y. and Kasper, D. L. (2010) How bacterial carbohydrates influence the adaptive immune system Annu. Rev. Immunol. 28, 107-10
7. Avci, F. Y., Li, X., Tsuji, M., and Kasper, D. L. (2011) A mechanism for glycoconjugate vaccine activation of the adaptive immune system and its implications for vaccine design Nat. Med. 17 (12) 1602-1610
8. Astronomo, R. D. and Burton, D. R. (2010) Carbohydrate vaccines: Developing sweet solutions to sticky situations? Nat. Rev. Drug Discov. 9, 308-324
9. Taylor, C. M. and Roberts, I. S. (2005) Capsular polysaccharides and their role in virulence Contrib. Microbiol. 12, 55-66
10. Calix, J. J., Porambo, R. J., Brady, A. M., Larson, T. R., Yother, J., Abeygunwardana, C., and Nahm, M. H. (2012) Biochemical, genetic, and serological characterization of two capsule subtypes among Streptococcus pneumoniae serotype 20 strains: discovery of a new pneumococcal serotype J. Biol. Chem. 27885-27894
11. Delrieu, I., Yaro, S., Tamekloe, T. A., Njanpop-Lafourcade, B. M., Tall, H., Jaillard, P., Quedraogo, M. S., Badziclou, K., Sanou, O., Drabo, A., Gessner, B. D., Kambou, J. L., and Mueller, J. E. (2011) Neisseria meningitidis serogroup X meningitis in Togo and Burkina Faso PLoS One 6 (5) e19513
12. Yother, J. (2011) Capsules of Streptococcus pneumoniae and other bacteria: Paradigms for polysaccharide biosynthesis and regulation Annu. Rev. Microbiol. 65, 563-581
13. Cieslewicz, M. J., Chaffin, D., Glusman, G., Kasper, D., Madan, A., Rodrigues, S., Fahey, J., Wessels, M. R., and Rubens, C. E. (2005) Structural and genetic diversity of Group B Streptococcus capsular polysaccharides Infect. Immun. 73 (5) 3096-3103
14. Woodward, R., Yi, W., Li, L., Zhao, G., Eguchi, H., Sridhar, P. R., Guo, H., Song, J. K., Motari, E., Cai, L., Kelleher, P., Liu, X., Han, W., Zhang, W., Ding, Y., Li, M., and Wang, P. G. (2010) In vitro bacterial polysaccharide biosynthesis: Defining the functions of Wzy and Wzz Nat. Chem. Biol. 6, 418-423
15. Coutinho, A. and Möller, G. (1973) B cell mitogenic properties of thymus-independent antigens Nat. New Biol. 245 (140) 12-14
16. Biggelaar, A. H. J. v. d. and Pomat, W. S. (2012) Immunization of newborns with bacterial conjugate vaccines Vaccine 1-6
17. Ada, G. and Isaacs, D. (2003) Carbohydrate-protein conjugate vaccines Clin. Microbiol. Infect. 9, 79-85
18. Weintraub, A. (2003) Immunology of bacterial polysaccharide antigens Carbohydr. Res. 338, 2539-2547
19. Mitchison, N. A. (1971) The carrier effect in the secondary response to haptenprotein conjugates. I. Measurement of the effect with transferred cells and objections to the local environment hypothesis Eur. J. Immunol. 1, 10-17
20. Mitchison, N. A. (1971) The carrier effect in the secondary response to haptenprotein conjugates. II. Cellular cooperation Eur. J. Immunol. 1, 18-27
21. Schneerson, R., Barrera, O., Sutton, A., and Robbins, J. B. (1980) Preparation, characterization, and immunogenicity of Haemophilus influenzae type b polysaccharide-protein conjugates J. Exp. Med. 152, 361-376
22. L.Trotter, C., McVernon, J., Ramsay, M. E., Whitney, C. G., Mulholland, E. K., Goldblatt, D., Hombach, J., and Kieny, M.-P. (2008) Optimizing the use of conjugate vaccines to prevent disease caused by Haemophilus influenzae type b, Neisseria meningitidis, and Streptococcus pneumoniae Vaccine 26, 4434-4445
23. Harding, C. V., R. W. Roof, P. M. A., and Unanue, E. R. (1991) Effects of pH and polysaccharides on peptide binding to class II major histocompatibility complex molecules Proc. Natl. Acad. Sci. U.S.A. 88, 2740-2744
24. 197 conjugate vaccine co-localizes with MHC II on the antigen processing cell surface Vaccine 27, 3137-3144
25. Guttormsen, H.-K., Sharpe, A. H., Chandraker, A. K., Brigtsen, A. K., Sayegh, M. H., and Kasper, D. L. (1999) Cognate stimulatory B cell-T cell recruited by glycoconjugate vaccines interactions are critical for T cell help Infect. Imm. 67 (12) 6375-6384
26. Galli-Stampino, L., Meinjohanns, E., Frische, K., Meldal, M., Jensen, T., Werdelin, O., and Mouritsen, S. (1997) T cell recognition of tumor-associated carbohydrates: The nature of the glycan moiety plays a decisive role in determining glycopeptide immunogenicity Cancer Res. 57, 3214-3222
27. Werdelin, O., Meldal, M., and Jensen, T. (2002) Processing of glycans on glycoprotein and glycopeptide antigens in antigenpresenting cells Proc. Natl. Acad. Sci. U.S.A. 99 (15) 9611-9613
28. Haurum, J. S., Arsequell, G., Lellouch, A. C., Wong, S. Y. C., Dwek, R. A., McMichael, A. J., and Elliott, T. (1994) Recognition of carbohydrate by Major Histocompatibility Complex class 1-restricted, glycopeptide-specific cytotoxic T lymphocytes J. Exp. Med. 180, 734-744
29. Morelli, L., Poletti, L., and Lay, L. (2011) Carbohydrates and immunology: Synthetic oligosaccharide antigens for vaccine formulation Eur. J. Org. Chem. 5723-5777
30. Kabanova, A., Margarit, I., Berti, F., Romano, M. R., Grandi, G., Bensi, G., Chiarot, E., Proietti, D., Swennen, E., Cappelletti, E., Fontania, P., Casini, D., Adamo, R., Pinto, V., Skibinski, D., Capoa, S., Buffi, G., Gallotta, M., Christ, W. J., Campbell, A. S., Pena, J., Seebergerd, P. H., Rappuoli, R., and Costantino, P. (2011) Evaluation of a Group A Streptococcus synthetic oligosaccharide as vaccine candidate Vaccine 29, 104-114
31. Safari, D., Dekker, H. A. T., Joosten, J. A. F., Michalik, D., Souza, A. C. d., Adamo, R., Lahmann, M., Sundgren, A., Oscarson, S., Kamerling, J. P., and Snippe, H. (2008) Identification of the smallest structure capable of evoking opsonophagocytic antibodies against Streptococcus pneumoniae type 14 Vaccine 76 (10) 4615-4623
32. Johnson, M. A. and Bundle, D. R. (2013) Designing a new antifungal glycoconjugate vaccine Chem. Soc. Rev. 42 (10) 4327-4444
33. Buskas, T., Thompson, P., and Boons, G.-J. (2009) Immunotherapy for cancer: Synthetic carbohydrate-based vaccines Chem. Commun. 5335-5349
34. Ingale, S., Wolfert, M. A., Gaekwad, J., Buskas, T., and Boons, G.-J. (2007) Robust immune responses elicited by a fully synthetic three-component vaccine Nat. Chem. Biol. 3 (10) 663-667
35. Xin, H., Dziadek, S., Bundle, D. R., and Cutler, J. E. (2008) Synthetic glycopeptide vaccines combining b-mannan and peptide epitopes induce protection against candidiasis Proc. Natl. Acad. Sci. U.S.A. 105 (36) 13526-13531
36. El-Manzalawy, Y., Dobbs, D., and Honavar, V. (2008) On evaluating MHC-II binding peptide prediction methods Plos One 3 (9) e3268
37. Chung, D. R., Kasper, D. L., Panzo, R. J., Chitnis, T., Grusby, M. J., Sayegh, M. H., and Tzianabos, A. O. (2003) CD4+ T cells mediate abscess formation in intraabdominal sepsis by an IL-17-dependent mechanism J. Immunol. 170 (4) 1958-1963
38. Tzianabos, A. O. and Kasper, D. L. (2002) Role of T cells in abscess formation Curr. Opin. Microbiol. 5 (1) 92-96
39. Stephen, T. L., Niemeyer, M., Tzianabos, A. O., Kroenke, M., Kasper, D. L., and Kalka-Moll, W. M. (2005) Effect of B7-2 and CD40 signals from activated antigen presenting cells on the ability of zwitterionic polysaccharides to induce T cell stimulation Infect. Immun. 73 (4) 2184-2189
40. Tzianabos, A. O., Finberg, R. W., Wang, Y., Chan, M., Onderdonk, A. B., Jennings, H. J., and Kasper, D. L. (2000) T cells activated by zwitterionic molecules prevent abscesses induced by pathogenic bacteria J. Biol. Chem. 275, 6733-6740
41. Duan, J., Avci, F. Y., and Kasper, D. L. (2008) Microbial carbohydrate depolymerization by antigen-presenting cells: Deamination prior to presentation by the MHCII pathway Proc. Natl. Acad. Sci. U.S.A. 105 (13) 5183-5188
42. Wang, J. Y., Kalka-Moll, W. M., Roehrl, M. H., and Kasper, D. L. (2000) Structural basis of the abscess-modulating polysaccharide A2 from Bacteroides fragilis Proc. Natl. Acad. Sci. U.S.A. 97, 13478-134783
43. Cobb, B. A. and Kasper, D. L. (2008) Characteristics of carbohydrate antigen binding to the presentation protein HLA-DR Glycobiology 18 (9) 707-718
44. Kalka-Moll, W. M., Tzianabos, A. O., Bryant, P. W., Niemeyer, M., Ploegh, H. L., and Kasper, D. L. (2002) Zwitterionic polysaccharides stimulate T cells by MHC class II-dependent interactions J. Immunol. 169 (11) 6149-6153
45. Cobb, B. A., Wang, Q., Tzianabos, A. O., and Kasper, D. L. (2004) Polysaccharide processing and presentation by the MHCII pathway Cell 117, 677-687
46. Silva, R. A. D., Wang, Q., Chidley, T., Appulage, D. K., and Andreana, P. R. (2009) Immunological response from an entirely carbohydrate antigen: Design of synthetic vaccines based on Tn-PS A1 conjugates J. Am. Chem. Soc. 131, 9622-9623
47. Ashkenazi, S., Passwell, J. H., Harlev, E., Miron, D., Dagan, R., Farzan, N., Ramon, R., Majadly, F., Bryla, D. A., Karpas, A. B., Robbins, J. B., and Schneerson, R. (1999) Safety and immunogenicity of Shigella sonnei and Shigella flexneri 2a O-specific polysaccharide conjugates in children J. Infect. Dis. 179, 1565-1568
48. Gallorini, S., Berti, F., Mancuso, G., Cozzi, R., Tortoli, M., Volpini, G., Telford, J. L., Beninati, C., Maione, D., and Wack, A. (2009) Toll-like receptor 2 dependent immunogenicity of glycoconjugate vaccines containing chemically derived zwitterionic polysaccharides Proc. Natl. Acad. Sci. U.S.A. 106 (41) 17481-17486
49. Gallorini, S., Berti, F., Parente, P., Baronio, R., Aprea, S., D'Oro, U., Pizza, M., Telford, J. L., and Wack, A. (2007) Introduction of zwitterionic motifs into bacterial polysaccharides generates TLR2 agonists able to activate APCs J. Immunol. 179, 8208-8215
50. Wack, A. and Gallorini, S. (2008) Bacterial polysaccharides with zwitterionic charge motifs: Toll-like receptor 2 agonists, T cell antigens or both? Immunopharmacol. Immunotoxicol. 30 (4) 761-770
51. Petrovsky, N. and Aguilar, J. C. (2004) Vaccine adjuvants: Current state and future trends Immunol. Cell. Biol. 82, 488-496
52. Rhee, J. H., Lee, S. E., and Kim, S. Y. (2012) Mucosal vaccine adjuvants update Clin. Exp. Vaccine Res. 1, 50-63
53. McKee, A. S., Munks, M. W., and Marrack, P. (2007) How do adjuvants work? Important considerations for new generation adjuvants Immunity 27, 687-690
54. Gupta, R. K. (1998) Aluminum compounds as vaccine adjuvants Adv. Drug Delivery Rev. 32, 155-172
55. Reese, T. A., Liang, H.-E., Tager, A. M., Luster, A. D., Rooijen, N. V., Voehringer, D., and Locksley, R. M. (2007) Chitin induces accumulation in tissue of innate immune cells associated with allergy Nature 447, 92-96
56. Li, X., Min, M., Du, N., Gu, Y., Hode, T., Naylor, M., Chen, D., Nordquist, R. E., and Chen, W. R. (2013) Chitin, chitosan, and glycated chitosan regulate immune responses: The novel adjuvants for cancer vaccine Clin. Dev. Immunol. 2013, 387023
57. Cooper, P. D., McComb, C., and Steele, E. J. (1991) The adjuvanticity of Algammulin, a new vaccine adjuvant Vaccine 9 (6) 408-415
58. Chan, G. C.-F., Chan, W. K., and Sze, D. M.-Y. (2009) The effects of β-glucan on human immune and cancer cells J. Hematol. Oncol. 2 (25 10.1186/1756-8722-2-25
59. Sheets, M. A., Unger, B. A., Giggleman G.F., Jr., and R.Tizard, I. (1991) Studies of the effect of acemannan on retrovirus infections: Clinical stabilization of feline leukemia virus-infected cats Mol. Biother. 3 (1) 41-45
60. Allison, A. C. and Gregoriadis, G. (1976) Liposomes as immunological adjuvants Recent Results Cancer Res. 56, 58-64
61. Smith, K., Peter, K., Andersen, L., and Christensen, D. (2012) Cationic liposomal vaccine adjuvants in animal challenge models: Overview and current clinical status Expert Rev. Vaccines 11 (5) 562-577
62. Singh, M., Kazzaz, J., Ugozzoli, M., Baudner, B., Pizza, M., Giuliani, M., Hawkins, L. D., Otten, G., and O'Hagan, D. T. (2012) MF59 oil-in-water emulsion in combination with a synthetic TLR4 agonist (E6020) is a potent adjuvant for a combination Meningococcus vaccine Hum. Vaccin. Immunother. 8 (4) 486-490
63. Petersson, P., Hedenskog, M., Alves, D., Brytting, M., Schröder, U., Linde, A., and Lundkvist, Å. (2010) The Eurocine® L3 adjuvants with subunit influenza antigens induce protective immunity in mice after intranasal vaccination Vaccine 28, 6491-6497
64. Drane, D., Gittleson, C., Boyle, J., and Maraskovsky, E. (2007) ISCOMATRIX adjuvant for prophylactic and therapeutic vaccines Expert Rev. Vaccines 6, 761-772
65. Kuehn, M. J. and Kesty, N. C. (2005) Bacterial outer membrane vesicles and the host-pathogen interaction Genes Dev. 19, 2645-2655
66. Huang, Y.-L., Hung, J.-T., Cheung, S. K. C., Lee, H.-Y., Chu, K.-C., Li, S.-T., Lin, Y.-C., Ren, C.-T., Cheng, T.-J. R., Hsu, T.-L., Yu, A. L., Wu, C.-Y., and Wong, C.-H. (2013) Carbohydrate-based vaccines with a glycolipid adjuvant for breast cancer Proc. Natl. Acad. Sci. U.S.A. 110 (7) 2517-2522
67. Long, E. M., Millen, B., Kubes, P., and Robbins, S. M. (2009) Lipoteichoic acid induces unique inflammatory responses when compared to other Toll-Like Receptor 2 ligands Plos One 4 (5) e5601
68. Roman, M., Martin-Orozco, E., Goodman, J. S., Nguyen, M. D., Sato, Y., Ronaghy, A., Kornbluth, R. S., Richman, D. D., Carson, D. A., and Raz, E. (1997) Immunostimulatory DNA sequences function as T helper-1-promoting adjuvants Nat Med. 3 (8) 849-854
69. Matyas, G. R., Mayorov, A. V., Rice, K. C., Jacobson, A. E., Cheng, K., Iyer, M. R., Li, F., Beck, Z., Janda, K. D., and Alving, C. R. (2013) Liposomes containing monophosphoryl lipid A: A potent adjuvant system forinducing antibodies to heroin hapten analogs Vaccine http://dx.doi.org/10.1016/j.vaccine. 2013.04.027
70. Chea, E. K., Fernández-Tejada, A., Damani, P., Adams, M. M., Gardner, J. R., Livingston, P. O., Ragupathi, G., and Gin, D. Y. (2012) Synthesis and preclinical evaluation of QS-21 variants leading to simplified vaccine adjuvants and mechanistic probes J. Am. Chem. Soc. 134, 13448-13457
71. Elson, C. O. (1992) Cholera Toxin as a mucosal adjuvant: Effects of H-2 Major Histocompatibility Complex and Ips genes Infect. Imm. 60 (7) 2874-2879
72. Leach, S., Clements, J. D., Kaim, J., and Lundgren, A. (2012) The adjuvant double mutant Escherichia coli Heat Labile Toxin enhances IL-17A production in human T cells specific for bacterial vaccine antigens Plos One 7 (12) e51718
73. Pizza, M., Fontana, M. R., Giuliani, M. M., Domenighini, M., Magagnoli, C., Giannelli, V., Nucci, D., Hole, W., Manetti, R., and Rappuoli, R. (1994) A genetically detoxified derivative of heat-labile Escherichia coli enterotoxin induces neutralizing antibodies against the A subunit J. Exp. Med. 180, 2147-2153
74. Wang, H., Paton, J. C., Herdman, B. P., Rogers, T. J., Beddoe, T., and Paton, A. W. (2013) The B subunit of an AB5 toxin produced by Salmonella enterica Serovar Typhi up-regulates chemokines, cytokines, and adhesion molecules in human macrophage, colonic epithelial, and brain microvascular endothelial cell lines Infect. Immun. 81 (3) 673-683
75. Kozako, T., Arima, N., Yoshimitsu, M., Honda, S.-I., and Soeda, S. (2012) Liposomes and nanotechnology in drug development: Focus on oncotargets Int. J. Nanomed. 7, 4943-4951
76. Rappuoli, R. and Aderem, A. (2011) A 2020 vision for vaccines against HIV, tuberculosis and malaria Nature 473, 463-469
77. Guo, Z. and Wang, Q. (2009) Recent development in carbohydrate-based cancer vaccines Curr. Opin. Chem. Biol. 13, 608-617
78. Bongat, A. F. G., Saksena, R., Adamo, R., Fujimoto, Y., Shiokawa, Z., Peterson, D. C., Fukase, K., Vann, W. F., and Kováč, P. (2010) Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant Glycoconj. J. 27, 69-77
79. Lakshminarayanana, V., Thompson, P., Wolfert, M. A., Buskas, T., Bradley, J. M., Pathangey, L. B., Madsen, C. S., Cohen, P. A., Gendler, S. J., and Boons, G.-J. (2012) Immune recognition of tumor-associated mucin MUC1 is achieved by a fully synthetic aberrantly glycosylated MUC1 tripartite vaccine Proc. Natl. Acad. Sci. U.S.A. 109 (1) 261-266
80. Verez-Bencomo, V., Fernandez-Santana, V., Hardy, E., Toledo, M. E., RodrIguez, M. C., Heynngnezz, L., Rodriguez, A., Baly, A., Herrera, L., Izquierdo, M., Villar, A., Valdes, Y., Cosme, K., Deler, M. L., Montane, M., Garcia, E., Ramos, A., Aguilar, A., Medina, E., Torano, G., Sosa, I., Hernandez, I., MartInez, R., Muzachio, A., Carmenates, A., Costa, L., Cardoso, F., Campa, C., Diaz, M., and Roy, R. (2004) A Synthetic Conjugate polysaccharide vaccine against Haemophilus influenzae type b Science 305, 522-525
81. Pozsgay, V. (2008) Recent developments in synthetic oligosaccharide-based bacterial vaccines Curr. Top. Med. Chem. 8, 126-140
82. Roy, R. (Ed.) ((2008) Carbohydrate-Based Vaccines, ACS Symposium Series, Vol. 989, pp 36-70, American Chemical Society, Washington, DC.
83. Costantino, P., Rappuoli, R., and Berti, F. (2011) The design of semi-synthetic and synthetic glycoconjugate vaccines Expert Opin. Drug Disc. 6 (10) 1045-1067
84. Imberty, A. and Perez, S. (2000) Structure, conformation, and biodynamics of bioactive oligosaccharides: Theoretical approaches and experimental validations Chem. Rev. 100, 4567-4588
85. Wang, C.-C., Kulkarni, S. S., Lee, J.-C., Luo, S.-Y., and Hung, S.-C. (2008) Regioselective one-pot protection of glucose Nat. Protocols 3 (1) 97-113
86. Zhu, X. and Schmidt, R. R. (2009) New principles for glycoside-bond formation Angew. Chem., Int. Ed. 48, 1900-1934
87. Crotti, S. and Adamo, R. (2013) New strategies for the synthesis of bio-medically relevant oligosaccharides: Recent updates on 1,2-cis-O- glycosylation and α-O-Sialylation Curr. Org. Synth. 10.2174/ 15701794113109990056
88. Kröck, L., Esposito, D., Castagner, B., Wang, C., Bindschädler, P., and Seeberger, P. H. (2012) Streamlined access to conjugation-ready glycans by automated synthesis Chem. Sci. 2012 (3) 1617-1622
89. Ganesh, N. V., Fujikawa, K., Tan, Y. H., Stine, K. J., and Demchenko, A. V. (2012) HPLC-assisted automated oligosaccharide synthesis Org. Lett. 14 (12) 3036-3039
90. Werz, D. B., Ranzinger, R., Herget, S., Adibekian, A., Lieth, C. W. v. d., and Seeberger, P. H. (2007) Exploring the structural diversity of mammalian carbohydrates ("glycospace") by statistical databank analysis ACS Chem. Biol. 2 (10) 685-691
91. Hsu, C.-H., Hung, S.-C., Wu, C.-Y., and Wong, C.-H. (2011) Toward automated oligosaccharide synthesis Angew. Chem., Int. Ed. 50, 11872-11923
92. Robbins, J. B., Kubler-Kielb, J., Vinogradov, E., Mocca, C., Pozsgay, V., Shiloach, J., and Schneerson, R. (2008) Synthesis, characterization, and immunogenicity in mice of Shigella sonnei O-specific oligosaccharide-core- protein conjugates Proc. Natl. Acad. Sci. U.S.A. 106 (19) 7974-7978
93. Kubler-Kielb, J., Vinogradov, E., LagergaÌŠrd, T., Ginzberg, A., King, J. D., Preston, A., Maskell, D. J., Pozsgay, V., Keith, J. M., Robbins, J. B., and Schneerson, R. (2011) Oligosaccharide conjugates of Bordetella pertussis and bronchiseptica induce bactericidal antibodies, an addition to pertussis vaccine Proc. Natl. Acad. Sci. U.S.A. 108 (10) 4087-4092
94. Theillet, F. X., Simenel, C., Guerreiro, C., Phalipon, A., Mulard, L. A., and Delepierre, M. (2011) Effects of backbone substitutions on the conformational behavior of Shigella flexneri O-antigens: Implications for vaccine strategy Glycobiology 21 (1) 109-121
95. Adamo, R., Romano, M. R., Berti, F., Leuzzi, R., Tontini, M., Danieli, E., Cappelletti, E., Cakici, O. S., Swennen, E., Pinto, V., Brogioni, B., Proietti, D., Galeotti, C. L., Lay, L., Monteiro, M. A., Scarselli, M., and Costantino, P. (2012) Phosphorylation of the synthetic hexasaccharide repeating unit is essential for the induction of antibodies to Clostridium difficile PSII cell wall polysaccharide ACS Chem. Biol. 7 (8) 1420-1428
96. Bernardes, G. J. L., Castagner, B., and Seeberger, P. H. (2009) Combined approaches to the synthesis and study of glycoproteins ACS Chem. Biol. 4 (9) 703-713
97. Grayson, E. J., Bernardes, G. J. L., Chalker, J. M., Boutureira, O., Koeppe, J. R., and Davis, B. G. (2011) A coordinated synthesis and conjugation strategy for the preparation of homogeneous glycoconjugate vaccine candidates Angew. Chem. Intl. Ed. 4127-4132 (50) 4127-4132
98. Adamo, R., Nilo, A., Castagner, B., Boutureira, O., Berti, F., and Bernardes, G. J. L. (2013) Synthetically defined glycoprotein vaccines: Current status and future directions Chem. Sci. 4, 2995-3008
99. Hu, Q.-Y., Allan, M., Adamo, R., Quinn, D., Zhai, H., Wu, G., Clark, K., Zhou, J., Ortiz, S., Wang, B., Danieli, E., Crotti, S., Tontini, M., Brogioni, G., and Berti, F. (2013) Synthesis of a well-defined glycoconjugate vaccine by a tyrosine-selective conjugation strategy Chem. Sci. 10.1039/C3SC51694F
100. Terra, V. S., Mills, D. C., Yates, L. E., Abouelhadid, S., Cuccui, J., and Wren, B. W. (2012) Recent developments in bacterial protein glycan coupling technology and glycoconjugate vaccine design J. Med. Microbiol. 61 (7) 919-926
101. Faridmoayer, A., Fentabil, M. A., Mills, D. C., Klassen, J. S., and Feldman, M. F. (2007) Functional characterization of bacterial oligosaccharyltransferases involved in O-linked protein glycosylation J. Bacteriol. 189 (22) 8088-8098
102. Kowarik, M., Numao, S., Feldman, M. F., Schulz, B. L., Callewaert, N., Kiermaier, E., Catrein, I., and Aebi, M. (2008) N-linked glycosylation of folded proteins by the bacterial oligosaccharyltransferase Science 314 (5802) 1148-1150
103. Ihssen, J., Kowarik, M., Dilettoso, S., Tanner, C., Wacker, M., and Thony-Meyer, L. (2010) Production of glycoprotein vaccines in Escherichia coli Microb. Cell. Fact 9 (61 10.1186/1475-2859-9-61
104. Wacker, M., Feldman, M. F., Callewaert, N., Kowarik, M., Clarke, B. R., Pohl, N. L., Hernandez, M., Vines, E. D., Valvano, M. A., Whitfield, C., and Aebi, M. (2006) Substrate specificity of bacterial oligosaccharyltransferase suggests a common transfer mechanism for the bacterial and eukaryotic systems Proc. Natl. Acad. Sci. U.S.A. 103 (18) 7088-7093
105. Fisher, A. C., Haitjema, C. H., Guarino, C., Celik, E., Endicott, C. E., Reading, C. A., Merritt, J. H., Ptak, A. C., Zhang, S., and De Lisa, M. P. (2011) Production of secretory and extracellular N-linked glycoproteins in Escherichia coli Appl. Environ. Microbiol. 77, 871-881