Application of β-1,4-galactosyltransferase in the synthesis of complex branched-chain oligosaccharide mimics of fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

Abstract

The chemoenzymic synthesis is described of β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→O[CH₂]₃O→4)-β-D-Glcp-(1→OCH₂CH[double bond, length half m-dash]CH₂) 32 and β-D-Galp-(1→4)-β-D-GlcpNAc-(1→ O[CH₂]₃O→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→O[CH₂]₃O→4)-β-D-Glcp-(1→OCH₂- CH[double bond, length half m-dash]CH₂) 33, representing hexa- and octasaccharide mimics of fragments of the Streptococcus pneumoniae type 14 polysaccharide. In a chemical approach the intermediate linear oligosaccharide mimics 30 and 31 were synthesized, wherein both terminal and non-terminal N-acetyl-β-D-glucosamine residues were not yet galactosylated. The alkyl-bridged derivatives were found to be good acceptor substrates for bovine milk β-1,4-galactosyltransferase. Reaction of the anomeric allyl functions with cysteamine under UV-irradiation gave the corresponding 3-(2-aminoethylthio)propyl glycosides 34 and 35, suitable for further coupling of the oligosaccharide mimics to protein carriers.

References

1. T. J. Mitchell and P. W. Andrew, in Molecular and Clinical Aspects of Bacterial Vaccine Development, ed. D. A. A. Ala'Aldeen and C. E. Hormaeche, Wiley, Chichester, 1995, p. 93.
2. D. L. Klein and R. W. Ellis, in New Generation Vaccines, ed. M. M. Levine, G. C. Woodrow, J. B. Kaper and G. S. Cobon, Marcel Dekker Inc., New York, 1997, p. 503.
3. R. Austrian, Rev. Infect. Dis., 1989, 11, S598.
4. P. C. Appelbaum, Clin. Infect. Dis., 1992, 15, 77.
5. R. F. Breiman, J. C. Butler, F. C. Tenover, J. A. Elliot and R. R. Facklam, JAMA, 1994, 271, 1831.
6. J. B. Robbins, R. Austrian, C.-J. Lee, S. C. Rastogi, G. Schiffman, J. Henrichsen, P. H. Mäkela, C. V. Broome, R. R. Facklam, R. H. Tiesjema and J. C. Parke, Jr., J. Infect. Dis., 1983, 148, 1136.
7. D. M. Musher, Clin. Infect. Dis., 1992, 14, 801.
8. E. A. de Velasco, A. F. M. Verheul, J. Verhoef and H. Snippe, Microbiol. Rev., 1995, 59, 591.
9. J. B. Robbins and R. Schneerson, J. Infect. Dis., 1990, 161, 821.
10. G. T. Rijkers, E. A. M. Sanders, M. A. Breukels and B. J. M. Zegers, Rev. Med. Microbiol., 1996, 7, 3.
11. B. Lindberg, J. Lönngren and D. A. Powell, Carbohydr. Res., 1977, 58, 177.
12. M. R. Wessels, V. Pozsgay, D. L. Kasper and H. J. Jennings, J. Biol. Chem., 1987, 262, 8262.
13. S. H. Landesman and G. Schiffman, Rev. Infect. Dis., 1981, 3, S184.
14. R. G. Colling, T. C. Pearson and J. C. Brown, Infect. Immun., 1983, 41, 205.
15. J. Thiem, FEMS Microbiol. Rev., 1995, 16, 193.
16. C.-H. Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., Int. Ed. Engl., 1995, 34, 521.
17. T. A. Beyer, J. E. Sadler, J. I. Rearick, J. C. Paulson and R. L. Hill, Adv. Enzymol. Relat. Areas Mol. Biol., 1981, 52, 23.
18. S. David, C. Augé and C. Gautheron, Adv. Carbohydr. Chem. Biochem., 1991, 49, 175.
19. M. M. Palcic, O. P. Srivastava and O. Hindsgaul, Carbohydr. Res., 1987, 159, 315.
20. J. Niggemann, J. P. Kamerling and J. F. G. Vliegenthart, Bioorg. Med. Chem., 1998, in the press.
21. C. R. Geren, S. C. Magee and K. E. Ebner, Arch. Biochem. Biophys., 1976, 172, 149.
22. M. M. Palcic, L. D. Heerze, M. Pierce and O. Hindsgaul, Glycoconjugate J., 1988, 5, 49.
23. S.-C. Ats, J. Lehmann and S. Petry, Carbohydr. Res., 1992, 233, 141.
24. S.-C. Ats, J. Lehmann and S. Petry, Carbohydr. Res., 1994, 252, 325.
25. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg and G. Magnusson, J. Org. Chem., 1988, 53, 5629.
26. A. G. Kalivretenos and K. Nakanishi, J. Org. Chem., 1993, 58, 6596.
27. H. Lönn, Carbohydr. Res., 1985, 139, 105.
28. P. Konradsson, U. E. Udodong and B. Fraser-Reid, Tetrahedron Lett., 1990, 31, 4313.
29. K. Takeo, K. Nagayoshi, K. Nishimura and S. Kitamura, J. Carbohydr. Chem., 1994, 13, 1159.
30. E. M. Nashed and C. P. J. Glaudemans, J. Org. Chem., 1987, 52, 5255.
31. R. R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 1994, 50, 21.
32. H. Paulsen and M. Paal, Carbohydr. Res., 1984, 135, 53.
33. F. A. W. Koeman, J. W. G. Meissner, H. R. P. van Ritter, J. P. Kamerling and J. F. G. Vliegenthart, J. Carbohydr. Chem., 1994, 13, 1.
34. R. U. Lemieux, T. Takeda and B. Y. Chung, in Synthetic Methods for Carbohydrates, ed. H. S. El Khadem, ACS Symposium Series 39, American Chemical Society, Washington, DC, 1976, p. 90.
35. O. Kanie, S. C. Crawley, M. M. Palcic and O. Hindsgaul, Carbohydr. Res., 1993, 243, 139.
36. U. Brodbeck and K. E. Ebner, J. Biol. Chem., 1966, 241, 762.
37. H. Babad and W. Z. Hassad, J. Biol. Chem., 1966, 241, 2672.
38. C. Unverzagt, H. Kunz and J. C. Paulson, J. Am. Chem. Soc., 1990, 112, 9308.
39. R. T. Lee and Y. C. Lee, Carbohydr. Res., 1974, 37, 193.