Linking carbohydrates to proteins using N-(2,2-dimethoxyethyl)-6- hydroxy hexanamide

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11783-11792

  Zhang, Jian ^a   Yergey, Alfred ^b   Kowalak, Jeffrey ^b   Kováč, Pavol ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

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

Author keywords

Antigen; Neoglycoconjugate; Reductive Amination; Vibrio cholerae

Indexed keywords

ACETAL DERIVATIVE; ANTIGEN; BACTERIAL POLYSACCHARIDE; CARBOHYDRATE; GLYCOCONJUGATE; HAPTEN; LYSINE; MONOSACCHARIDE; PROTEIN; VACCINE;

AMINATION; ARTICLE; DRUG SYNTHESIS; GLYCOSYLATION; IMMUNOGENICITY; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; SPECTROMETRY; STEREOCHEMISTRY; VIBRIO CHOLERAE;

BACTERIA (MICROORGANISMS); GALLUS GALLUS; VIBRIO CHOLERAE;

EID: 0032564013     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83039-1     Document Type: Article

References (31)

1. Avery, O. T.; Goebel, W. F. J. Exp. Med. 1929, 50, 521-533.
2. Goebel, W. F. J. Exp. Med. 1939, 69, 353-363.
3. Goebel, W. F. J. Exp. Med. 1940, 70, 33-48.
4. Schneerson, R.; Barrera, O.; Sutton, A.; Robbins, J. B. J. Exp. Med. 1980, 152, 361-376.
5. Gray, G. R. Arch. Biochem. Biophys. 1974, 163, 426-428.
6. Gray, G. R.; Schwartz, B. A.; Kamicker, B. J. Prog. Clin. Biol. Res. 1978, 23, 583-94.
7. Dick Jr, W. E.; Beurret, M. Glycoconjugates of bacterial carbohydrate antigens. In Conjugate Vaccines; Cruse, J. M.; Lewis Jr, R. E. Eds.; Krager: Basel, 1989; Vol. 10; pp. 48-114.
8. Lee, R. T.; Lee, Y. C. Carbohydr. Res. 1979, 77, 149-156.
9. Lee, R. T.; Lee, Y. C. Biochemistry 1980, 19, 156-163.
10. Lee, R. T.; Wong, T.-C.; Lee, R.; Yue, L.; Lee, Y. C. Biochemistry 1989, 28, 1856-1861.
11. Pozsgay, V. Glycoconjugate J. 1993, 10, 133-141.
12. Lee, Y. C.; Lee, R. T. Neoglycoconjugates: Preparation and Application; Academic Press: New York, 1994.
13. Pozsgay, V. Angew. Chem. Int. Ed. Engl. 1998, 37, 138-142.
14. Zhang, J.; Kováč, P. Tetrahedron Lett. 1998, 39, 1091-1094.
15. Kenne, L.; Unger, P.; Wehler, T. J. Chem. Soc. Perkin Trans. 1 1988, 1183-1196.
16. Gotoh, M.; Barnes, C. L.; Kováč, P. Carbohydr. Res. 1994, 260, 203-218.
17. Wilstermann, M.; Magnusson, G. Carbohydr. Res. 1995, 272, 1-7.
18. Ness, R. K.; Fletcher, H. G.; Hudson, C. S. J. Am. Chem. Soc. 1950, 72, 2200-2205.
19. Schmidt, R. R. Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
20. Garegg, P. J.; Norberg, T. Acta Chem. Scand. 1979, B33, 116-118.
21. Kováč, P.; Taylor, R. B. Carbohydr. Res. 1987, 167, 153-173.
22. Lubineau, A.; Drouillat, B. J. Carbohydr. Chem. 1997, 16, 1179-1186.
23. Wang, J.; Zhang, J.; Miller, C. E.; Villenuve, S.; Ogawa, Y.; Lei, P.-s.; Lafaye, P.; Nato, F.; Karpas, A.; Bystrický, S.; Szu, S. C.; Robbins, J. B.; Kováč, P.; Fournier, J.-M.; Glaudemans, C. P. J. J. Biol. Chem. 1998, 273, 2777-2783.
24. Eichler, E.; Kihlberg, J.; Bundle, D. Glycoconjugate J. 1991, 8, 69-74.
25. Peters, T.; Bundle, D. R. Can. J. Chem. 1989, 67, 497-502.
26. Peters, T.; Bundle, D. R. Can. J. Chem. 1989, 67, 491-496.
27. Zhang, J.; Kováč, P. Carbohydr. Res. 1997, 300, 329-339.
28. Hache, R. J. G.; Wiskocil, R.; Vasa, M.; Roy, R. N.; Lau, P. C. K.; Deeley, R. G. J. Biol. Chem. 1983, 258, 4556-4564.
29. Lei, P.-s.; Ogawa, Y.; Kováč, P. Carbohydr. Res. 1996, 281, 47-60.
30. Lei, P.-s.; Ogawa, Y.; Kováč, P. Carbohydr. Res. 1995, 279, 117-131.
31. Chen, R. F. J. Biol. Chem. 1967, 242, 173-181.