Peptide dissociation in solution or bound to a polymer: Comparative solvent effect

Tetrahedron

Volumn 60, Issue 42, 2004, Pages 9417-9424

  Malavolta, Luciana ^a   Nakaie, Clóvis R ^a  

^a FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Peptide; Polarity; Polymer; Solubility; Solvent

Indexed keywords

PEPTIDE; POLYMER; RESIN; SOLVENT; WATER;

ACIDITY; ALKALINITY; ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; DISSOCIATION; DISSOLUTION; POLARIZATION; PRIORITY JOURNAL; SOLUBILIZATION; SOLVATION;

EID: 4544311194     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.013     Document Type: Article

References (56)

1. A.R. Katritzky, D.C. Fara, Y. Hongfang, and K. Tämm Chem. Rev. 104 2004 175 198
2. C. Reichardt Chem. Rev. 94 1994 2319 2358
3. Y. Markus Chem. Soc. Rev. 22 1993 409 416
4. O. Pytela Coll. Czech. Chem. Commun. 53 1988 1333 1423
5. E.M. Cilli, E. Oliveira, R. Marchetto, and C.R. Nakaie J. Org. Chem. 61 1996 8992 9000
6. L. Malavolta, E. Oliveira, E.M. Cilli, and C.R. Nakaie Tetrahedron 58 2002 4383 4394
7. E.M. Cilli, R. Marchetto, S. Schreier, and C.R. Nakaie Tetrahedron Lett. 38 1997 517 520
8. E.M. Cilli, R. Marchetto, S. Schreier, and C.R. Nakaie J. Org. Chem. 64 1999 9118 9123
9. R. Marchetto, S. Schreier, and C.R. Nakaie J. Am. Chem. Soc. 115 1993 11042 11043
10. V. Gutmann The Donor-Acceptor Approach to Molecular Interactions 1978 Plenum New York
11. V. Gutmann Electrochim. Acta 21 1976 661 670
12. E. Oliveira, E.M. Cilli, A. Miranda, G.N. Jubilut, A. Albericio, A. Andreu, A.C.M. Paiva, S. Schreier, and C.R. Nakaie Eur. J. Org. Chem. 21 2002 3686 3694
13. G. Barany, and R.B. Merrifield The Peptides 1980 Academic Press New York p 1
14. (b) Stewart, J. M.; Young, J. D.; Solid Phase Peptide Synthesis; Pierce Chemical Company: Rockford, 1984; Vol. III.
15. G.B. Fields, and R.L. Noble Int. J. Pept. Protein Res. 35 1990 161 214
16. R.L. Letsinger, J.L. Finnan, G.A. Heavner, and W.B. Lunsford J. Am. Chem. Soc. 85 1975 3278 3279
17. V.D. Amarnath, and A. Broom Chem. Rev. 77 1977 183 217
18. J.M. Fréchet, and C. Schuerch J. Am. Chem. Soc. 93 1971 492 498
19. U. Zehavi, and A. Patchornik J. Am. Chem. Soc. 95 1973 5673 5678
20. G. Jung, and A.G. BeckSickinger Angew. Chem. Int. Ed. Eng. 31 1992 367 383
21. K.S. Lam, M. Lebl, and V. Krchanak Chem. Rev. 97 1997 411 448
22. K.S. Lam, S.E. Salmon, E.M. Hersh, V.J. Hruby, W.M. Kazmierski, and R.J. Knapp Nature 354 1991 82 84
23. M. Fridkin, A. Patchornik, and E. Kachalski J. Am. Chem. Soc. 88 1966 3164 3166
24. J.M.J. Frechet Tetrahedron 37 1981 663 683
25. P.H.H. Hermkens, H.C.J. Ottenheijm, and D. Rees Tetrahedron 52 1996 4527 4554
26. L.A. Thompson, and J.A. Ellman Chem. Rev. 95 1996 555 600
27. D.J. Gordon, and S.C. Meredith Biochemistry 42 2003 475 485
28. S. Srisailam, T.K.S. Kumar, D. Rajalingam, K.M. Kathir, H.S. Sheu, F.J. Jan, P.C. Chao, and C. Yu J. Biol. Chem. 278 2003 17701 17709
29. A. Banerjee, S.K. Maji, M.G.B. Drew, D. Haldar, and A. Banerjee Tetrahedron Lett. 44 2003 335 339
30. R. Zahn, A. Liu, T. Lührs, R. Riek, C. von Schroetter, F.L. Garcia, M. Billeter, L. Calzolai, G. Wider, and K. Wüthrich Proc. Natl Acad. Sci. 97 2000 145 150
31. M.R. Nilsson, L.L. Nguyen, and D.P. Raleigh Anal. Biochem. 288 2001 76 82
32. P.G. Pietta, P.F. Cavallo, K. Takahashi, and G.R. Marshall J. Org. Chem. 39 1974 44 48
33. K.J. Jensen, J. Alsina, M.F. Songster, J. Vágner, F. Albericio, and G. Barany J. Am. Chem. Soc. 120 1998 5441 5452
34. J.B. Dame, J.L. Williams, T.F. McCtchan, J.L. Weber, R.A. Wirtz, W.T. Hockmeyer, W.L. Maloy, J.D. Haynes, I. Schneider, D. Roberts, G.S. Sanders, E.P. Reddy, C.L. Diggs, and L.H. Miller Science 225 1984 593 599
35. H. Abe, K. Kawasaki, and H. Nakanishi Jpn Biochem. Soc. 132 2002 863 874
36. J.J. Balbach, Y. Tshii, O.N. Antzutkin, R.D. Leapman, N.W. Rizzo, F. Dyda, J. Reed, and R. Tyeko Biochemistry 39 2000 13748 13759
37. F. Rabanal, J.M. Tusell, L. Sastre, M.R. Quintero, M. Cruz, D. Grillo, M. Pons, F. Alberício, J. Serratosa, and E. Giralt J. Pept. Sci. 8 2002 578 588
38. G.R. Matsueda, and J.M. Stewart Peptides 2 1981 45 50
39. V.K. Sarin, S.B.H. Kent, and R.B. Merrifield J. Am. Chem. Soc. 102 1980 5463 5470
40. J.P. Tam, and Y.A. Lu J. Am. Chem. Soc. 117 1995 12058 12063
41. R. Marchetto, A. Etchegaray, and C.R. Nakaie J. Braz. Chem. Soc. 3 1992 30 37
42. A.F.M. Burton Chem. Rev. 75 1975 731 753
43. J.H. Hildebrand Chem. Rev. 44 1949 37 45
44. K. Dimroth, C. Reichardt, T. Siepmann, and F. Bohlman Liebigs Ann. Chem. 661 1963 1 37
45. A.J. Parker Chem. Rev. 69 1969 1 32
46. M. Narita, J.Y. Chen, H. Sato, and Y. Kim Bull. Chem. Soc. Jpn 58 1985 2494 2501
47. J.L. Brown, K. Kato, J. Silver, and S.G. Nathenso Biochemistry 13 1974 3174 3178
48. J.L. Meek, and Z.L. Rossetti J. Chromatogr. 211 1981 15 28
49. S. Sen, D. Dash, S. Pasha, and S.K. Brahmachari Protein Sci. 12 2003 953 962
50. E.P. Vieira, H. Hermel, and H. Möhwald Biochim. Biophys. Acta 1645 2003 6 14
51. M. Narita, S. Honda, H. Umeyama, and S. Obana Bull. Chem. Soc. Jpn 61 1988 281 284
52. N. Hirota-Nakaoka, K. Hasegawa, H. Naiki, and Y. Goto J. Biochem. 134 2003 159 164
53. W.J. Cheong, Y.I. Keum, and J.H. Ko Bull. Kr. Chem. Soc. 23 2002 65 70
54. S. Chen, and R. Wetzel Protein Sci. 10 2001 887 891
55. F. Formaggio, A. Bettio, V. Moretto, M. Crisma, C. Toniolo, and Q.B. Broxterman J. Pept. Sci. 9 2003 461 466
56. I. Sirangelo, F.D. Piaz, C. Malmo, M. Casillo, L. Birolo, P. Pucci, G. Marino, and G. Irace Biochemistry 42 2003 312 319