Synthesis of a functionalized GDP-analogue designed for anti-GDP antibody production

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2321-2324

  Vincent, Stéphane ^a   Mioskowski, Charles ^a   Lebeau, Luc ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; CARRIER PROTEIN; FUNCTIONAL GROUP; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE; GUANOSINE DIPHOSPHATE; HAPTEN; POLYCLONAL ANTIBODY;

ANIMAL EXPERIMENT; ANTIBODY PRODUCTION; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; IMMUNIZATION; NONHUMAN; RABBIT; SIGNAL TRANSDUCTION; SYNTHESIS;

EID: 0032537164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00144-0     Document Type: Article

References (44)

1. 1. Hille, B. Neuron 1992, 9, 187-195.
2. 2. Birnbaumer, L.; Abramowitz, J.; Brown, A.M. Biochim. Biophys. Acta 1990, 1031, 163-224.
3. 3. Neer, E.J. Cell 1995, 80, 249-257.
4. 4. Neubig, R.R. FASEB J. 1994, 8, 939-946.
5. 5. Yarfitz, S.; Hurley, J.B. J. Biol. Chem. 1994, 269, 14329-14332.
6. 6. Hepler, J.R.; Gilman, A.G. TiBS 1992, 17, 383-387.
7. 7. Lamb, T.D.; Pugh, E.N.J. TiNS 1992, 15, 291-298.
8. 8. Kuo, J.F.; Greengard, P. J. Biol. Chem. 1970, 245, 4067-4073.
9. 9. Kamidate, T.; Kinkou, T.; Watanabe, H. Chem. Lett. 1996, 237-238.
10. 10. Gilman, A.G. Proc. Natl. Acad. Sci. USA 1970, 67, 305-312.
11. 11. Steiner, A.L.; Kipnis, D.M.; Utiger, R.; Parker, C.W. Proc. Natl. Acad. Sci. USA 1969, 64, 367-373.
12. 12. Piall, E.M.; Aherne, G.W.; Marks, V. Anal. Biochem. 1986, 154, 276-281.
13. 13. Piall, E.M.; Curtin, N.J.; Aherne, G.W.; Harris, A.L.; Marks, V. Anal. Biochem. 1989, 177, 347-352.
14. 14. Cerpovicz, P.F.; Ochs, R.S. Anal. Biochem. 1991, 192, 197-202.
15. 15. Pradelles, P.; Grassi, J.; Chabardes, D.; Guiso, N. Anal. Chem. 1989, 61, 447-453.
16. 16. Yamamoto, T.; Shimizu, H.; Kato, T.; Nagatsu, T. Anal. Biochem. 1984, 142, 395-399.
17. 17. Maessen, J.G.; van der Vusse, G.J.; York, M.; Kootstra, G. Clin. Chem. 1988, 34, 1087-1090.
18. 18. de Korte, D.; Haverkort, W.A.; Roos, D.; van Gennip, A.H. Clin. Chim. Acta 1985, 148, 185-196.
19. 19. Di Pierro, D.; Tavazzi, B.; Perno, C.F.; Bartolini, M.; Balestra, E.; Calio, R.; Giardina, B.; Lazzarino, G. Anal. Biochem. 1995, 231, 407-412.
20. 20. De Lean, A.; Rouleau, D.; Lefkowitz, R.J. Life Sci. 1983, 33, 943-954.
21. 21. Goujon, L.; Brossette, T.; Dereudre-Bosquet, N.; Creminon, C.; Clayette, P.; Dormont, D.; Mioskowski, C.; Lebeau, L.; Grassi, J. Submitted.
22. 22. Bredehorst, R.; Ferro, A.; Hilz, H. Eur. J. Biochem. 1978, 82, 105-113.
23. 23. Yanachkov, I.; Pan, J.Y.; Wessling-Resnick, M.; Wright, G.E. Mol. Pharmacol. 1997, 51, 47-51.
24. 24. Yount, R.G.; Babcock, D.; Ballantyne, W.; Ojala, D. Biochemistry 1971, 10, 2484-2489.
25. 25. Yount, R.G. Adv. Enzymol. 1975, 43, 1-56.
26. 26. Ma, Q.F.; Babbitt, P.C.; Kenyon, G.L. J. Am. Chem. Soc. 1988, 110, 4060-4061.
27. 27. Hopwood, D. Histochem. 1969, 17, 151-161.
28. 28. Lehrer, S.S. Biochem. Biophys. Res. Commun. 1972, 48, 967-976.
29. 29. Sun, T.T.; Traut, R.R.; Kahan, L. J. Mol. Biol. 1974, 87, 509-522.
30. 30. Gulland, M.J.; Overend, W.G. J. Chem. Soc. 1948, 1380-1382.
31. 31. Lipkin, D.; Phillips, B.; Hunter, W.H. Tetrahedron Lett. 1959, 18-21.
32. 32. Vincent, S.; Mons, S.; Lebeau, L.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 7527-7530.
33. 33. Regiochemistry was determined by X-ray cristallography. Vincent, S.; Grenier, S.; Salesse, C.; Mioskowski, C.; Lebeau, L. In preparation
34. 34. Saady, M.; Lebeau, L.; Mioskowski, C. J. Org. Chem. 1995, 60, 2946-2947.
35. 35. Hughes, D.L.; Reamer, R. A.; Bergan, J.J.; Grabowski, E.J.J. J. Am. Chem. Soc. 1988, 110, 6487-6491.
36. 36. Hughes, D.L. Organic Reactions 1992, 42, 335-656.
37. 37. Mitsunobu, O. Synthesis 1981, 1-28.
38. 38. Campbell, D.A.; Bermack, J.C. J. Org. Chem. 1994, 59, 658-660.
39. 39. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642.
40. 40. Tsunoda, T.; Ito, S. J. Syn. Org. Chem. Jpn 1997, 55, 631-641.
41. 41. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chem. Lett. 1994, 539-542.
42. 3) 8.91 and 8.88 (2s, 1H); 7.70 (s, 1H); 7.60-7.15 (m, 15H); 6.23 and 6.14 (2d, J = 2.3 Hz, 1H); 6.19 and 6.03 (2s, 1H); 5.47 and 5.42 (2dd, J = 2.3, 6.4 Hz, 1H); 5.03 (2dd, J = 3.2, 6.4 Hz, 1H); 4.71 (s, 2H); 4.60 (t, J = 6.3 Hz, 2H); 4.51-4.05 (m, 5H); 3.74 (t, J = 6.3 Hz, 2H); 3.65-3.45 (m, 6H); 3.28 (t, J = 5.2 Hz, 2H); 2.00 (s, 3H). IR (film) 2923; 2872; 2106, 1743; 1690; 1613; 1574; 1530; 1493; 1431; 1360; 1223; 1097; 1028; 760.
43. 3) 8.93 and 8.91 (2s, 1H); 7.80, 7.75, 7.72 and 7.68 (4s, 1H); 7.60-7.15 (m, 35H); 6.16 and 6.08 (2m, 1H); 6.10, 5.90 and 5.97 (3s, 1H); 5.17 (m, 1H); 5.02-4.35 (m, 16H); 4.25 and 3.95 (2m, 2H); 3.72 (t, J= 6.4 Hz, 2H); 3.65-3.45 (m, 6H); 3.27 (t, J = 5.0 Hz, 2H). IR (film) 3061; 3031; 2926; 2105; 1692; 1611; 1572; 1529; 1493; 1454; 1359; 1273; 1216; 1094; 1016.
44. +.