Synthesis of a branched heptose- and kdo-containing common tetrasaccharide core structure of haemophilus influenzae lipopolysaccharides via a l,6-anhydro-l-glycero-β-d-manno-heptopyranose intermediate

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7780-7788

  Bernlind, Christian ^a   Oscarson, Stefan ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000450523     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9808573     Document Type: Article

References (37)

1. Turk, D. C. J. Med. Microbiol. 1984,18, 1.
2. Lindberg, B.; Kenne, L. In The Polysaccharides; Aspinall, G. O., Ed.; Academic Press Inc.: New York, 1983; Vol. 2, p 287.
3. Lindberg, A. A.; Pillai, S. In Developments in Biological Standardization; Brown, F., Ed.; 1996; Vol. 87, p 59.
4. Chong, P.; Chan, N.; Kandil, A. A.; Tripet, B.; James, O.; Yang, Y.-R; Shi S.-P.; Klein, M. Infect. Immun. 1997, 65, 4918.
5. Kandil, A. A.; Chan, N.; Klein, M.; Chong, P. Glycoconjugate J. 1997, 14, 13.
6. Phillips, N. J.; Apicella, M. A.; McLeod Grifiiss, J.; Gibson, B. W. Biochemistry 1992, 31, 4515.
7. Phillips, N. J.; Apicella, M. A.; McLeod Griffiss, J.; Gibson, B. W. Biochemistry 1993, 32, 2003.
8. Schweda, E. K. H.; Hegedus, O. E.; Borelli, S.; Lindberg, A. A.; Weiser, J. N.; Maskell, D. J.; Moxon, E. R. Carbohydr. Res. 1993,246, 319.
9. Schweda, E. K. H.; Jansson, P.-E.; Moxon, E. R.; Lindberg, A. A. Carbohydr. Res. 1995, 272, 213.
10. Phillips, N. J.; McLaughlin, R.; Miller, T. J.; Apicella, M. A.; Gibson, B. W. Biochemistry 1996, 35, 5937.
11. Gu, X.-X.; Tsai, C.-M.; Ueyama, T.; Barenkamp, S. J.; Bobbins, J. B.; Lim, D. J. J. Bacterial. Infect. Immun. 1996, 645, 4047.
12. Schweda, E. K. H.; Jonasson, J. A.; Jansson, P.-E. J. Bacterial. 1995, 177, 5316.
13. Di fabio, J. L.; Michon, F.; Brisson, J. R.; Jennings, H. J. Can. J. Chem. 1990, 68, 1029.
14. Garegg, P. J.; Oscarson, S.; Ritzén, H.; Szönyi, M. Carbohydr. Res. 1992, 228, 121.
15. Bernlind, C.; Oscarson, S. Carbohydr. Res. 1997, 297, 251.
16. Bernlind, C. Licentiate Thesis, Stockholm University, 1996.
17. Söderman, P.; Jansson, P. E.; Widmalm, G. J. Chem. Soc., Perkin Trans. 2, in press.
18. Shapiro, D.; Rabinsohn, Y.; Diver-Haber, A. Biochem. Biophys. Res. Commun. 1969, 37, 28.
19. Spijker, N. M,; van Boeckel, C. A. A. Angew. Chetn., Int. Ed. Engl. 1991, 30, 180.
20. Lafont, D.; Boullanger, P.; Banoub, J.; Descotes, G. Can. J. Chem. 1990, 68, 828.
21. Lafont, D.; Boullanger, P.; Cadas, O.; Descotes, G. Synthesis 1989, 191.
22. Oscarson, S. Top. Curr. Chem. 1997, 186, 171.
23. Bernlind, C. Doctoral Dissertation, Stockholm University, 1998.
24. Angyal, S. J.; Beveridge, R. J. Carbohydr. Res. 1978, 65, 229.
25. Boons, G. J. P. H. Doctoral Dissertation, Leiden University, 1991.
26. Dziewiszek, K.; Zamojski, A. Carbohydr. Res. 1986, 150, 163.
27. Castro, B. Bull. Soc. Chim. Fr. 1986, 1533.
28. Blomberg, C.; Hartog, F. A. Synthesis 1977, 18.
29. Ishihara, K.; Hideki, K; Yamamoto, H. J. Org. Chem. 1993, 55, 3791
30. Ness, R. K.; Fletcher, H. G., Jr.; Hudson, C. S. J. Am. Chem. Soc. 1950, 72, 2200.
31. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
32. Fügedi, P.; Garegg, P. J. Carbohydr. Res. 1986, 149, c9.
33. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
34. Björndal, H.; Hellerqvist, C. G.; Lindberg, B.; Svensson, S. Angew. Chem., Int. Ed. Engl. 1970, 9, 610.
35. Ekelöf, K.; Oscarson, S. Carbohydr. Res. 1995, 278, 289.
36. Ekelöf, K. Doctoral dissertation, Stockholm University, 1996.
37. Connor, D. S.; Klein, G. W.; Taylor, G. N. Org. Synth. 1972, 52, 16.