Determination of site-site distance and site concentration within polymer beads: A combined swelling-electron paramagnetic resonance study

Journal of Organic Chemistry

Volumn 70, Issue 12, 2005, Pages 4561-4568

  Marchetto, Reinaldo ^a   Cilli, Eduardo M ^a   Jubilut, Guita N ^b   Schreier, Shirley ^c   Nakaie, Clovis R ^b  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CARBOXYLIC ACIDS; ELECTRON SPIN RESONANCE SPECTROSCOPY; REACTION KINETICS; RESINS;

COUPLING REACTIONS; POLYMER SOLVATION; POLYMER SWELLING; SITE CONCENTRATION;

POLYMER BLENDS;

2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL 4 AMINO 4 CARBOXYLIC ACID; BENZHYDRYL DERIVATIVE; BENZYLAMINE; COPOLYMER; DIVINYLBENZENE; POLYMER; STYRENE; TEMPOL; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; CALCULATION; CONCENTRATION (PARAMETERS); ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; REACTION TIME; SOLVATION; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; CHEMISTRY, PHYSICAL; ELECTRON SPIN RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PEPTIDES; POLYMERS;

EID: 20344366295     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0483318     Document Type: Article

References (82)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. (a) Barany, G.; Merrifield, R. B. The Peptides; Academic Press Inc.: New York, 1979; Vol. 2, pp 1-284.
3. (b) Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis; Pierce Chemical Co.: Rockford, IL, 1984.
4. (c) Fields, G. B.; Noble, R. L. Int. J. Peptide Protein Res. 1990, 35, 161.
5. (d) Kates, S. A., Albericio, F. Solid-Phase Synthesis. A Practical Guide; Marcel Dekker: New York, Basel, 2000; pp 275-330.
6. (e) Kent, S. B. H. Annu. Rev. Biochem. 1988, 57, 957.
7. (a) Fréchet, J. M.; Schuerch, C. J. Am. Chem. Soc. 1971, 93, 492.
8. (b) Zehavi, U.; Patchornik, A. J. Am. Chem. Soc. 1973, 95, 5673.
9. (c) Letsinger, R. L.; Finnan, J. L.; Heavner, G. A.; Lunsford, W. B. J. Am. Chem. Soc. 1975, 85, 3278.
10. (d) Amarnath, V., Broom, A. D. Chem. Rev. 1977, 77, 183.
11. (a) Hermkens, P. H. H.; Ottenheim, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527
12. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 95, 555,
13. (c) Hermkens, P. H. H.; Ottenheim, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
14. (a) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82.
15. (b) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
16. (c) Lam, K. S., Salmon, S. E., Hersh, E. M., Hruby, V. J., Kasmierski, W. M., Knapp, R. J. Nature 1991, 354, 82.
17. (a) Lebl, M. Biopolymers 1998, 47, 397.
18. (b) Kates, S. A.; McGuiness, B. F.; Blackburn, C.; Griffin, G. W.; Solé, N. A.; Barany, G.; Albericio, F. Biopolymers 1998, 47, 365.
19. (c) Meldal, M. In Methods in Enzymology: Solid-Phase Peptide Synthesis; Fields, G., Ed.; Academic Press: New York 1997; pp 83-103.
20. (a) Ludwick, A. G.; Jelinski, L. W.; Live, D.; Kintamar, A.; Dumais, J. J. J. Am. Chem. Soc. 1986, 108, 6493.
21. (b) Deber, C. M.; Lutek, M. K.; Heimer, E. P.; Felix, A. M. Peptide Res. 1989, 2, 184.
22. (c) Warrass, R.; Wieruszeski, M.; Bouitillon, C.; Lippens, G. J. Am. Chem. Soc 2000, 122, 1789.
23. (d) Furrer, J.; Piotto, M.; Bourdonneau, M.; Limal, D.; Guichard, G.; Elbayed, K.; Briand, J. P.; Bianco, A. J. Am. Chem. Soc. 2001, 123, 4130.
24. (e) Gambs, C.; Dickerson T. J.; Mahajan, S.; Pasternack L. B.; Janda, K. D. J. Org. Chem. 2003, 68, 3673.
25. (f) Zhao, T. J.; Beckham, H. W.
26. (g) Zhao, T. J.; Beckham, H. W.; Gibson, H. W. Macromolecules 2003 13, 4833.
27. (a) Milton, R. C. L.; Milton, S. C. F.; Adams, P. A. J. Am. Chem. Soc. 1990, 112, 5039.
28. (b) Hendrix, J. C., Halverson, K. J., Jarret, J. T.; Lansbury, P. T., Jr. J. Org. Chem. 1990, 55, 4517.
29. (c) Yan, B. Acc. Chem. Res. 1998, 31, 621.
30. (a) Li, Y. H.; Chan, L. M.; Tyler, L.; Moody, R. T.; Himel, C. M.; Hercules, D. M. J. Am. Chem. Soc. 1975, 97, 3118.
31. (b) Shea, K. J.; Sassaki, D. Y.; Stoddarard, G. J. Macromolecules 1989, 22, 1722.
32. (c) Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.
33. (a) Kress, J.; Rose, A.; Frey, J. G.; Brocklesby, W. S.; Ladlow, M.; Mellor, G. W.; Bradley, M. Chem. Eur. J. 2001, 7, 3880.
34. (b) Rademann, J.; Barth, M.; Brock, R.; Egelhaaf, H. J.; Jung, G. Chem. Eur. J. 2001, 7, 3884.
35. (c) Kress, J., Zanaletti, R.; Rose, A.; Frey, J. G.; Brockesby, W. S.; Ladlow, M.; Bradley, M. J. Comb. Chem. 2003, 5, 28.
36. (a) Regen, S. L. J. Am. Chem. Soc. 1974, 96, 5275.
37. (b) Ward, T. C.; Brooks, J. T. Macromolecules 1974, 7, 207.
38. (c) Vaino, A. R.; Goodin, D. B.; Janda, K. D. J. Comb. Chem. 2000, 2, 330.
39. (a) Nakaie, C. R.; Schreier, S.; Paiva, A. C. M. Braz. J. Med. Biol. Res. 1981, 14, 173.
40. (b) Marchetto, R.; Schreier, S.; Nakaie, C. R. J. Am. Chem. Soc. 1993, 117, 11042.
41. (c) Barbosa, S. R.; Cilli, E. M.; Lamy-Freund, M. T.; Castrucci, A. M. L., Nakaie, C. R. FEBS Lett. 1999, 446, 45.
42. (d) Pertinhez, T. A.; Nakaie, C. R.; Carvalho, R. S. H.; Paiva, A. C. M.; Tabak, M.; Toma, E.; Schreier, S. Biopolymers 1977, 42, 821.
43. (e) Nakaie, C. R.; Silva, E. G.; Cilli, E. M.; Marchetto, R.; Schreier, S.; Paiva, T. B.; Paiva, A. C. M. Peptides 2002, 23, 65.
44. (f) Schreier, S.; Barbosa, S. R.; Casallanovo, F., Vieira, R. F. F., Cilli, E. M.; Paiva, A. C. M.; Nakaie, C. R. Biopolymers 2004, 74, 389.
45. (a) Smithe, M. L.; Nakaie, C. R.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 10555.
46. (b) Toniolo, C.; Valente, E.; Formaggio, F.; Crisma, M.; Pilloni, G.; Corvaja, C.; Toffoletti, A.; Martinez, G. V.; Hanson, M. P.; Millhauser, G. L.; George, C.; Flippen-Anderson, J. J. Pept. Sci. 1995, 1, 45.
47. (c) McNulty, J. C.; Silapie, J. L.; Carnevali, M.; Farrar, C. T.; Griffin, R. G.; Formaggio, F.; Crisma, M.; Toniolo, C.; Millhauser, G. L. Biopolymers 2000, 55, 479.
48. (d) Victor, K. G., Cafiso, D. S. Biophys. J. 2001, 81, 2241.
49. (e) Pispisa, B., Palleschi, L., Stella, M., Venanzi, M., Toniolo, C. J. Phys. Chem. B 1998, 102, 7890.
50. (a) Cilli, E. M.; Marchetto, R.; Schreier, S.; Nakaie, C. R. Tetrahedron Lett. 1997, 38, 517.
51. (b) Cilli, E. M.; Marchetto, R.; Schreier, S.; Nakaie, C. R. J. Org. Chem. 1999, 64, 9118.
52. (c) Ribeiro, S. C. F., Schreier, S., Nakaie, C. R., Cilli, E. M. Tetrahedron Lett. 2001, 42, 3243.
53. (d) Oliveira, E.; Cilli, E. M.; Miranda, A.; Jubilut, G. N.; Albericio, F.; Andreu, A.; Paiva, A. C. M.; Schreier, S.; Tominaga, M.; Nakaie, C. R. Eur. J. Org. Chem. 2002, 21, 3686.
54. (a) Katritzky, A. R., Fara, D. C., Hongfang, Y., Tämm, K. Chem. Rev. 2004, 104, 175,
55. (b) Markus, Y. Chem. Soc. Rev. 1993, 22, 409.
56. (c) Reichardt, C. Chem. Rev. 1994, 94, 2319.
57. (c) Pytela, O. Collect. Czech. Chem. Commun. 1988, 53, 1333.
58. (d) Burton, A. F. M. Chem. Rev. 1975, 75, 731.
59. (a) Sarin, V. K.; Kent, S. B. H.; Merrifield, R. B. J. Am. Chem. Soc. 1980, 102, 5463.
60. (b) Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 3, 4202.
61. (c) Tam, J. P.; Lu, Y. A. J. Am. Chem. Soc. 1995, 117, 12058.
62. (d) Pugh, K. C.; York, E. J.; Stewart, J. M. Int. J. Peptide Protein Res. 1992, 40, 208.
63. (a) Cilli, E. M.; Oliveira, E.; Marchetto, R.; Nakaie, C. R. J. Org. Chem. 1996, 61, 8992.
64. (b) Malavolta, L.; Oliveira, E.; Cilli, E. M.; Nakaie C. R. Tetrahedron 2002, 58, 4383.
65. (a) Gutmann, V. Electrochim. Acta 1976, 21, 661.
66. (b) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum Press: New York, 1978.
67. Malavolta, L.; Nakaie, C. R. Tetrahedron 2004, 60, 9417.
68. (a) Pietta, P. G.; Cavallo, P. F.; Takahashi, K.; Marshall, G. R. J. Org. Chem. 1974, 39, 44.
69. (b) Marchetto, R.; Etchegaray, A.; Nakaie, C. R. J. Braz. Chem. Soc. 1992, 3, 30.
70. Gisin, B. F. Anal. Chim. Acta 1972, 58, 248.
71. Gross, E., Meienhofer, J., Eds. Peptides: Analysis, Synthesis, Biology; Academic Press: New York, 1989; Vol. 1.
72. Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774.
73. Merrifield, B. R.; Littau, V. In Peptides 1968; Bricas, E., ed.; North-Holland Publishing Co.: Amsterdam, 1968; p 179.
74. (a) Taylor, J. S.; Leigh, J. S., Jr.; Cohn, M. Proc. Natl. Acad. Sci. U.S.A. 1969, 64, 219.
75. (b) Mchaourab, H. S.; Oh, K. J.; Fang, C. J.; Hubbell, W. L. Biochemistry 1997, 36, 307.
76. (a) Devaux, P., McConnell, H. M. J. Am. Chem. Soc. 1972; 94, 4475.
77. (b) Sackmann, E.; Träuble, H. J. Am. Chem. Soc. 1972, 94, 4482.
78. (c) Träuble, H. J.; Sackmann, E. J. Am. Chem. Soc. 1972, 94, 4492.
79. (d) Sackmann, E.; Träuble, H. J. Am. Chem. Soc. 1972, 94, 4499.
80. (a) Scandella, C. J.; Devaux, P.; McConnell, H. M. Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 2056.
81. (b) Sackmann, E.; Trauble, H.; Galla, H. J.; Overath, P. Biochemistry 1973, 12, 5360.
82. Irani, R. R.; Callis, C. F. Particle Size: Measurement, Interpretation and Application; Wiley: New York, 1963.