Conjugating low molecular mass carbohydrates to proteins 2. Recovery of excess ligand used in the conjugation reaction

Methods in Enzymology

Volumn 362, Issue , 2003, Pages 140-159

  Saksena, Rina ^a   Chernyak, Anatoly ^a   Poirot, Emmanuel ^a   Kováč, Pavol ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; GLYCOCONJUGATE; HAPTEN; LIGAND; OLIGOSACCHARIDE; PROTEIN; SCHIFF BASE; SYNTHETIC GLYCOCONJUGATE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONJUGATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; VIBRIO CHOLERAE;

VIBRIO; VIBRIO CHOLERAE;

EID: 0042528735     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(03)01011-5     Document Type: Article

References (42)

1. W. F. Goebel and O. T. Avery, J. Exp. Med. 50, 521 (1929).
2. O. T. Avery and W. F. Goebel, J. Exp. Med. 50, 533 (1929).
3. Y. C. Lee and R. T. Lee, "Neoglycoconjugates: Preparation and Application." Academic Press, New York, 1994.
4. P. Kováč (Ed.), "Synthetic Oligosaccharides: Indispensable Probes in the Life Sciences," Vol. 560. American Chemical Society, Washington, D.C., 1994.
5. M. Dubber and T. K. Lindhorst, Synthesis (2001).
6. J. Zhang, A. Yergey, J. Kowalak, and P. Kováč, Tetrahedron 54, 11783 (1998).
7. R. Roy, E. Katzenellenbogen and H. J. Jennings, Can. J. Biochem. Cell Biol. 62, 270 (1984).
8. A. Chernyak and P. Kováč, unpublished results.
9. G. T. Hermanson, "Bioconjugate Techniques." Academic Press, New York, 1996.
10. G. R. Gray, Methods Enzymol. 50, 155 (1978).
11. N. Jentoft and D. G. Dearborn, J. Biol. Chem. 254, 4359 (1979).
12. R. F. Borch, M. D. Berntein, and H. D. Durst, J. Am. Chem. Soc. 93, 2897 (1971).
13. C. F. Lane, in "Selections from the Aldrichimica Chemica Acta, " 1968-1982, p. 67. Aldrich Chemical Company, Milwaukee, WI, 1984.
14. L. F. Tietze, A. Goerlach, and M. Beller, Justus Liebigs Ann. Chem. 565 (1988).
15. L. F. Tietze, M. Arlt, M. Beller, K.-H. Glüsenkamp, E. Jähde, and M. F. Rajewsky, Chem. Ber. 124, 1215 (1991).
16. L. F. Tietze, C. Schröter, S. Gabius, U. Brinck, A. Goerlach-Graw, and H.-J. Gabius, Bioconjug. Chem. 2, 148 (1991).
17. J. Zhang and P. Kováč, Bioorg. Med. Chem. Lett. 9, 487 (1999).
18. J. Zhang, A. Yergey, J. Kowalak, and P. Kováč, Carbohydr. Res. 313, 15 (1998).
19. V. P. Kamath, P. Diedrich, and O. Hindsgaul, Glycoconjug. J. 13, 315 (1996).
20. Squaric acid dimethyl and diethyl esters are available from Aldrich Chemical Co. The analogous dibutyl ester is available from Acros Organics through Fisher Scientific.
21. K.-H. Glüsenkamp, W. Drosdziok, G. Eberle, E. Jähde, and M. F. Rajewsky, Z. Naturforsch. C. 46, 498 (1991).
22. S. Cohen and S. G. Cohen, J. Am. Chem. Soc. 88, 1533 (1966).
23. J. Zhang and P. Kováč, Carbohydr. Res. 321, 157 (1999).
24. A. Chernyak, A. Karavanov, Y. Ogawa, and P. Kováč, Carbohydr. Res. 330, 479 (2001).
25. D. R. Bundle, M. Gerken, and T. Peters, Carbohydr. Res. 174, 239 (1988).
26. T. Peters and D. R. Bundle, Can. J. Chem. 67, 497 (1989).
27. T. Peters and D. R. Bundle, Can. J. Chem. 67, 491 (1989).
28. P.-s. Lei, Y. Ogawa, and P. Kováč, Carbohydr. Res. 279, 117 (1995).
29. P.-s. Lei, Y. Ogawa, and P. Kováč, Carbohydr. Res. 281, 47 (1996).
30. J. Zhang and P. Kováč, Carbohydr. Res. 300, 329 (1997).
31. Y. Ogawa, P.-s., Lei, and P. Kováč, Carbohydr. Res. 288, 85 (1996).
32. Y. Ogawa, P.-s. Lei, and P. Kováč, Carbohydr. Res. 293, 173 (1996).
33. M. Gotoh and P. Kováč, J. Carbohydr. Chem. 13, 1193 (1994).
34. R. J. Ferrier and R. H. Furneaux, Methods Carbohydr. Chem. 8, 251 (1980).
35. T. Adachi, Y. Yamada, I. Inoue, and M. Saneyoshi, Synthesis 45 (1977).
36. J. Ohlsson and G. Magnusson, Carbohydr. Res. 329, 49 (2000).
37. H. C. Hansen and G. Magnusson, Carbohydr. Res. 307, 233 (1998).
38. M. Numata, M. Sugimoto, K. Koike, and T. Ogawa, Carbohydr. Res. 163, 209 (1987).
39. G. Solladie and C. Ziani-Cherif, J. Org. Chem. 58, 2181 (1993).
40. E. Petráková and J. Schraml, Collect. Czech. Chem. Commun. 48, 877 (1983).
41. N. E. Byramova, M. V. Ovchinnikov, L. V. Backinowsky, and N. K. Kochetkov, Carbohydr. Res. 124, C8 (1983).
42. R. Saksena, A. Chernyak, A. Karavanor, and P. Kováč, Methods Enzymol. 362 [10] (2003) (this volume).