Determination of the absolute amount of resin-bound hydroxyl or carboxyl groups for the optimization of solid-phase combinatorial and parallel organic synthesis

Analytical Chemistry

Volumn 71, Issue 20, 1999, Pages 4564-4571

  Yan, Bing ^a   Liu, Lina ^a   Astor, Catherine A ^a   Tang, Qing ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYL GROUP; HYDROXYL GROUP; NITRILE; PYRENE DERIVATIVE; QUINUCLIDINE; RESIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; SUPERNATANT; ULTRAVIOLET SPECTROSCOPY;

EID: 0032731283     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac990685p     Document Type: Article

References (39)

1. (a) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
2. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
3. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
4. (d) DeWitt, D. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
5. (e) Still, W. C. Acc. Chem. Res. 1996, 29, 155.
6. (f) Ellman, J. A. Acc. Chem. Res. 1996, 29, 132.
7. (g) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
8. (h) Balkenhohl, F.; Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
9. (i) Lam, K. S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411.
10. (a) Leznoff, C. C. Acc. Chem. Res. 1978, 11, 327.
11. (b) Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557.
12. (c) Frechet, J. M. J. Tetrahedron 1981, 37, 663.
13. (d) Hodge, P. In Synthesis and separations using functional polymers; Sherrington, D. D., Hodge, P., Eds.; Wiley: Chichester, 1988; Chapter 2.
14. (a) Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487.
15. (b) Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84.
16. (c) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82.
17. (a) Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
18. (b) Fontenot, J. D.; Ball, J. M.; Miller, M. A.; David, C. M.; Montelaro, R. C. Pept. Res. 1991, 4, 19.
19. (c) Garden, J., II; Tometsko, A. M. Anal. Biochem. 1972, 46, 216.
20. Krchnak, V.; Vagner, J.; Lebl, M. Int. J. Pept. Protein Res. 1988, 32, 415.
21. (e) Ngo, T. T. Appl. Biochem. Biotechnol. 1986, 13, 213.
22. (f) Sarin, V. K.; Kent, S. B. H.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 1981, 117, 147.
23. (g) Tyllianakis, P. E.; Kakabakos, S. E.; Evangelatos, G. P.; Ithakissios, D. S. Anal. Biochem. 1994, 219, 335.
24. (h) Chu, S. S.; Reich, S. H. Bioorg. Med. Chem. Lett. 1995, 5, 1053.
25. Yan, B.; Li, W. J. Org. Chem. 1997, 62, 9354.
26. (a) Kamato, K.; Takahashi M.; Terasima, K.; Nishijima M. J. Chromatogr., A 1994, 667, 113.
27. (b) Ramesha, C. S.; Pickett, W. C.; Murthy, D. V. K. J. Chromatogr. 1989, 491, 37.
28. (c) Goto, J.; Goto, N.; Shama, F.; Saito, M.; Komatsu, S.; Suzaki, K.; Nambara, T. Anal. Chim. Acta 1983, 147, 397.
29. Goto, J.; Saito, M.; Chikai, T.; Goto, N.; Nambara, T. J Chromatogr. 1983, 276, 289.
30. (a) Yan, B.; Kumaravel, G.; Anjaria, H.; Wu, A.; Petter, R.; Jewell, C. F., Jr.; Wareing, J. R. J. Org. Chem. 1995, 60, 5736.
31. (b) Yan, B.; Kumaravel, G. Tetrahedron 1996, 52, 843.
32. (c) Yan, B.; Fell, J. B.; Kumaravel, G. J. Org. Chem. 1996, 61, 7467.
33. (d) Yan, B.; Sun, Q.; Wareing, J. R.; Jewell, C. F. J. Org. Chem. 1996, 61, 8765.
34. Letsinger, R. L.; Kornet, M. J.; Mahadevan, V.; Jerina, D. M. J. Am. Chem. Soc. 1964, 86, 5163.
35. (a) Iwamura, M.; Ishikawa, T.; Koyama, Y.; Sakuma, K.; Iwamura, H. Tetrahedron Lett. 1987, 28, 679.
36. (b) Nimura, N.; Kinoshita, T.; Yoshida, T.; Uetake, A.; Nakai, C. Anal. Chem. 1988, 60, 2067.
37. (c) Yoshida, T.; Uetake, A.; Nakai, C.; Nimura, N.; Kinoshita, T. J. Chromatogr. 1988, 456, 421.
38. (d) Iohan, F.; Monder, C.; Cohen, S. J. Chromatogr. 1991, 564, 27.
39. (e) Schneede, J.; Ueland, P. M. Anal. Chem. 1992, 64, 315.