Synthetic Shigella Vaccines: A Carbohydrate - Protein Conjugate with Totally Synthetic Hexadecasaccharide Haptens

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 138-142

  Pozsgay, Vince ^a  

^a EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

Author keywords

Antigens; Carbohydrates; Oligosaccharides; Protecting groups; Vaccines

Indexed keywords

EID: 0031882559     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t     Document Type: Article

References (50)

1. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
2. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
3. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
4. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
5. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
6. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
7. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
8. Reviews: a) J. B. Robbins, R. Schneerson, S. Szu, V. Pozsgay in Vaccinia, Vaccination and Vaccinology: Jenner, Pasteur and their Successors (Eds.: S. Plotkin, B. Fantini), Elsevier, Paris, 1996, pp. 135-143; b) R. K. Sood, A. Fattom, V. Pavliak, R. B. Naso, Drug Discovery Today 1996, 1, 381-387; c) A. Fattom, Adv. Expt. Med. Biol. 1995, 383, 131-139; d) U. B. S. Sørensen, Danish Med. Bull. 1995, 42, 47-53; e) H. J. Jennings, R. K. Sood in Neoglycoconjugates. Preparation and Applications (Eds.: Y. C. Lee, R. T. Lee), Academic Press, New York, 1994, pp. 325-371; f) W. Egan, Ann. Rep. Med. Chem. 1993, 28, 257-265; g) P. R. Paradiso, K. Dermody, S. Pillai, Vaccine Res. 1993, 2, 239-248; h) H. J. Jennings, Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
9. For the development of this concept, see: a) K. Landsteiner, The specificity of serological reactions, Harvard University Press, Cambridge, 1970; b) W. F. Goebel, O. T. Avery, J. Exp. Med. 1929, 50, 521-531.
10. For the development of this concept, see: a) K. Landsteiner, The specificity of serological reactions, Harvard University Press, Cambridge, 1970; b) W. F. Goebel, O. T. Avery, J. Exp. Med. 1929, 50, 521-531.
11. R. Schneerson, O. Barrera, A. Sutton, J. B. Robbins, J. Exp. Med. 1980, 152, 361-376.
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13. See for example: a) D. Cohen, S. Ashkenazi, M. S. Green, M. Gdalevich, G. Robin, R. Slepon, M. Yavzori, N. Orr, C. Block, Y. Ashkenazi, J. Shemer, D. N. Taylor, T. L. Hale, J. D. Sadoff, D. Pavliakova, R. Schneerson, J. B. Robbins, Lancet 1997, 349, 155-159; b) D. Cohen, S. Ashkenazi, M. S. Green, Y. Lerman, R. Slepon, G. Robin, N. Orr, D. N. Taylor, J. C. Sadoff, C. Chu, J. Shiloach, R. Schneerson, J. B. Robbins, Infect. Immun. 1997, 64, 4074-4077.
14. See for example: a) D. Cohen, S. Ashkenazi, M. S. Green, M. Gdalevich, G. Robin, R. Slepon, M. Yavzori, N. Orr, C. Block, Y. Ashkenazi, J. Shemer, D. N. Taylor, T. L. Hale, J. D. Sadoff, D. Pavliakova, R. Schneerson, J. B. Robbins, Lancet 1997, 349, 155-159; b) D. Cohen, S. Ashkenazi, M. S. Green, Y. Lerman, R. Slepon, G. Robin, N. Orr, D. N. Taylor, J. C. Sadoff, C. Chu, J. Shiloach, R. Schneerson, J. B. Robbins, Infect. Immun. 1997, 64, 4074-4077.
15. For previous approaches to glycoconjugate vaccines against human pathogenic bacteria, see: a) E. Alonso de Velasco, A. F. M. Verheul, A. M. P. van Stein, H. A. T. Dekker, R. G. Feldman, I. M. Fernández, J. P. Kamerling, J. F. G. Vliegenthart, J. Verhoef, H. Snippe, Infect. Immun. 1994, 62, 799-808; b) C. C. A. M. Peeters, D. Evenberg, P. Hoogerhout, H. Käyhty, L. Saarinen, C. A. A. van Boeckel, G. A. van der Marel, J. H. van Boom, J. T. Poolman, ibid. 1992, 60, 1826-1833; c) A. F. M. Verheul, G. J. P. H. Boons, G. A. van der Marel, J. H. van Boom, H. J. Jennings, H. Snippe, J. Verhoef, P. Hoogerhout, J. T. Poolman, ibid. 1991, 59, 3566-3573; d) H. J. A. Jörbeck, S. B. Svenson, A. A. Lindberg, ibid. 1981, 32, 497-502.
16. For previous approaches to glycoconjugate vaccines against human pathogenic bacteria, see: a) E. Alonso de Velasco, A. F. M. Verheul, A. M. P. van Stein, H. A. T. Dekker, R. G. Feldman, I. M. Fernández, J. P. Kamerling, J. F. G. Vliegenthart, J. Verhoef, H. Snippe, Infect. Immun. 1994, 62, 799-808; b) C. C. A. M. Peeters, D. Evenberg, P. Hoogerhout, H. Käyhty, L. Saarinen, C. A. A. van Boeckel, G. A. van der Marel, J. H. van Boom, J. T. Poolman, ibid. 1992, 60, 1826-1833; c) A. F. M. Verheul, G. J. P. H. Boons, G. A. van der Marel, J. H. van Boom, H. J. Jennings, H. Snippe, J. Verhoef, P. Hoogerhout, J. T. Poolman, ibid. 1991, 59, 3566-3573; d) H. J. A. Jörbeck, S. B. Svenson, A. A. Lindberg, ibid. 1981, 32, 497-502.
17. For previous approaches to glycoconjugate vaccines against human pathogenic bacteria, see: a) E. Alonso de Velasco, A. F. M. Verheul, A. M. P. van Stein, H. A. T. Dekker, R. G. Feldman, I. M. Fernández, J. P. Kamerling, J. F. G. Vliegenthart, J. Verhoef, H. Snippe, Infect. Immun. 1994, 62, 799-808; b) C. C. A. M. Peeters, D. Evenberg, P. Hoogerhout, H. Käyhty, L. Saarinen, C. A. A. van Boeckel, G. A. van der Marel, J. H. van Boom, J. T. Poolman, ibid. 1992, 60, 1826-1833; c) A. F. M. Verheul, G. J. P. H. Boons, G. A. van der Marel, J. H. van Boom, H. J. Jennings, H. Snippe, J. Verhoef, P. Hoogerhout, J. T. Poolman, ibid. 1991, 59, 3566-3573; d) H. J. A. Jörbeck, S. B. Svenson, A. A. Lindberg, ibid. 1981, 32, 497-502.
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44. 2, CSA], ester hydrolysis (LiOH). and acidification (citric acid) in 78% overall yield.
45. 2, CSA], ester hydrolysis (LiOH). and acidification (citric acid) in 78% overall yield.
46. For our earlier approaches for the introduction of a terminal, aldehydo group-containing linker moiety, see a) V. Pozsgay, L. Trinh, J. Shiloach, J. B. Robbins, A. Donahue Rolfe, S. B. Calderwood, Bioconj. Chem. 1996, 7, 45-55. b) V. Pozsgay, Glycoconj. J. 1993, 10, 133-141.
47. For our earlier approaches for the introduction of a terminal, aldehydo group-containing linker moiety, see a) V. Pozsgay, L. Trinh, J. Shiloach, J. B. Robbins, A. Donahue Rolfe, S. B. Calderwood, Bioconj. Chem. 1996, 7, 45-55. b) V. Pozsgay, Glycoconj. J. 1993, 10, 133-141.
48. G. R. Gray, Arch. Biochem. Biophys. 1974, 163, 426-428. Reductive amination attaches the ω-aldehydoalkyl moiety to the epsi;-amino group of the lysine residues of proteins resulting in an epsi;-N-alkylated construct that preserves the original net charge of the protein (C. P. Stowell, Y. C. Lee, Adv. Carbohydr. Chem. Biochem. 1981, 37, 225-281).
49. G. R. Gray, Arch. Biochem. Biophys. 1974, 163, 426-428. Reductive amination attaches the ω-aldehydoalkyl moiety to the epsi;-amino group of the lysine residues of proteins resulting in an epsi;-N-alkylated construct that preserves the original net charge of the protein (C. P. Stowell, Y. C. Lee, Adv. Carbohydr. Chem. Biochem. 1981, 37, 225-281).
50. The MALDI-TOF mass spectra were recorded on a KRATOS MALDI III instrument operated at an accelerating voltage of 22 kV. The sample was dissolved in 0.1% trifluoroacetic acid and 50% acetonitrile and applied to the target sample in a sinapinic acid matrix. The molecular weight of HSA was measured as 66 350 Da.