Selective deprotection of phenacyl, benzyl and methyl esters of N-protected amino acids and dipeptides and N-protected amino acids benzyl ester linked to resins with bis(tributyltin) oxide

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1996, Pages 995-999

  Salomon, Claudio J ^a   Mata, Ernesto G ^a   Mascaretti, Oreste A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001338641     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000995     Document Type: Article

References (71)

1. For a recent review on chemical deprotection of esters functional groups, see: C. J. Salomon, E. G. Mata and O. A. Mascaretti, Tetrahedron, 1993, 49, 3691.
2. (a) T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, J. Wiley & Sons, New York, 1991;
3. (b) P. J. Kocienski, Protecting Groups, Georg Thieme Verlag, Stuttgart, 1994.
4. G. Barany and F. J. Albericio, J. Am. Chem. Soc., 1985, 107, 4936.
5. (a) C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Org. Chem., 1994, 59, 7259.
6. For preliminary communications see: (b) E. G. Mata and O. A. Mascaretti, Tetrahedron Lett., 1988, 29, 6893;
7. (c) C. J. Salomon, E. G. Mata and O. A. Mascaretti, Tetrahedron Lett., 1991, 32, 4239.
8. M. G. Pérez and M. S. Maier, Tetrahedron Lett., 1995, 36, 3311.
9. For the principles of chemical synthesis of peptides, see: (a) J. Jones, The Chemical Synthesis of Peptides, Clarendon Press, Oxford, 1994;
10. (b) M. Bodanszky, Principles of Peptide Synthesis, Springer-Verlag, Berlin, 1993;
11. (c) M. Bodanszky, Peptide Chemistry, Springer-Verlag, Berlin, 1993.
12. For reviews on solid-phase peptide synthesis, see: (a) G. Barany and R. B. Merrified, in The Peptides Analysis, Synthesis and Biology, E. Gross and J. Meienhofer, eds., Academic Press, New York, 1980, vol. 2, pp. 1-284;
13. (b) R. B. Merrifield, Science, 1986, 232, 341;
14. (c) J. M. Stewart and J. D. Young, Solid Phase Peptide Synthesis, 2nd edn., Pierce Chemical Company, Rockford, Illinois, 1984;
15. (d) E. W. Atherton and R. C. Sheppard, Solid Phase Synthesis: A Practical Approach, 1989, IRL Press, Oxford.
16. M. Namikoshi, B. Kundu and K. L. Rinehart, J. Org. Chem., 1991, 56, 5464.
17. P. Braun, H. Waldmann, W. Vogt and H. Kunz, Synlett, 1990, 105.
18. For a recent review on combinatorial synthesis, see: N. K. Terret, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 30, 8135 and references cited therein.
19. W. H. Moos and G. D. Green, Ann. Rep. Med. Chem., 1993, 28, 315.
20. G. Jung and A. G. Beck-Sickinger, Angew. Chem. Int. Ed. Engl., 1992, 31, 367.
21. (a) B. Bunin, M. Plunkett and J. Ellman, Proc. Natl. Acad. Sci. USA, 1994, 91, 4708;
22. (b) S. Hobbs DeWitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. Reynolds Cody and M. R. Pavia, Proc. Natl. Acad. Sci., USA, 1993, 90, 6909.
23. B. Déprez, X. Willard, L. Bourel, H. Coste, F. Hyafil and A. Tartar, J. Am. Chem. Soc., 1995, 117, 5405.
24. R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
25. (a) S. S. Wang, J. Am. Chem. Soc., 1973, 95, 1328;
26. (b) S. S. Wang, J. Org. Chem., 1975, 40, 1235;
27. (c) J. K. Chang, M. Shimizu and S. S. Wang, J. Org. Chem., 1976, 41, 3255.
28. (a) A. R. Mitchell, B. W. Erickson, M. N. Ryabtsev, R. S. Hodges and R. B. Merrifield, J. Am. Chem. Soc., 1976, 98, 7357;
29. (b) for a new synthetic route to Pam resin see: A. R. Mitchell, S. B. H. Kent, M. Engelhard and R. B. Merrifield, J. Org. Chem., 1978, 43, 2845.
30. (a) M. Mergler, R. Tanner, J. Gostelli and P. Grogg, Tetrahedron Lett., 1988, 29, 4005;
31. (b) M. Mergler, R. Nyfeler, R. Tanner, J. Gosteli and P. Grogg, Tetrahedron Lett., 1988, 29, 4009.
32. For a recent review of HF cleavage and deprotection procedures for peptides synthesized using a Boc/Bz strategy in SPPS, see: M. W, Pennington, in Peptide Synthesis Protocols, M. W. Pennington and B. M. Duran, eds., Humana Press Inc., Totowa, New Jersey, 1994, p. 41.
33. 1 strategy in SPPS, see: F. Dick, in Peptide Synthesis Protocols, M. W. Pennington and B. M. Duran, eds., Humana Press Inc., Totowa, New Jersey, 1994, p. 63.
34. For recent reviews on convergent solid-phase synthesis which also provides a comprehensive account of diverse methods for the cleavage of protected peptides from a diversity of solid supports, see: (a) P. L. Williams, F. Albericio and E. Giralt, Tetrahedron, 1993, 49, 11065;
35. (b) H. Benz, Synthesis, 1994, 337.
36. For a recent review of chromatographic techniques for the purification of protected peptide segments, see: M. Gairí, P. Lloyd-Williams, F. Albericio and E. Giralt, Int. J. Peptide Protein Res., 1995, 46, 119.
37. M. Mergler, in Peptide Synthesis Protocols, M. W. Pennington and B. M. Duran, eds., Humana Press Inc., Totowa, New Jersey, 1994, p. 287.
38. (a) J. M. Schlatter, R. M. Mazur and O. Goodmonson, Tetrahedron Lett., 1977, 2851;
39. (b) D. A. Jones, Tetrahedron Lett., 1977, 2853.
40. (a) G. M. Anantharamaiah and K. M. Sivanandalah, J. Chem. Soc., Perkin Trans. 1, 1977, 490;
41. (b) S. A. Khan and K. M. Sivanandalah, Synthesis, 1978, 750;
42. (c) A. M. Felix, E. P. Heimer, T. J. Lambros, C. Tzougraki and J. Meienhofer, J. Org. Chem., 1978, 43, 4194;
43. (d) B. ElAmin, G. M. Anantharamaiah, G. P. Royer and G. E. Means, J. Org. Chem., 1979, 44, 3442;
44. (e) M. K. Anwer, A. F. Spatola, C. D. Bossinger, E. Flanigan, R. C. Liu, D. B. Olsen and D. Stevenson, J. Org. Chem., 1983, 46, 3503;
45. (f) M. K. Anwer, R. E. Porter and A. F. Spatola, Int. J. Peptide Protein Res., 1987, 30, 489;
46. (g) S. Ram and R. E. Ehrenkaufer, Synthesis, 1988, 91;
47. (h) M. K. Anwer, D. B. Sherman, J. Gordon Roney and A. F. Spatola, J. Org. Chem., 1989, 54, 1284.
48. M. K. Anwer and A. F. Spatola, Tetrahedron Lett., 1992, 33, 3121.
49. F. Rabanal, E. Giralt and F. Albericio, Tetrahedron, 1995, 51, 1449.
50. For a recent paper on this methodology, see: P. L. Williams, A. Merzouk, F. Guibé, F. Albericio and E. Giralt, Tetrahedron Lett., 1994, 35, 4437.
51. For others relevant references of palladium catalysed hydrostannolytic cleavage in SPPS, see: (a) F. Guibé, O. Dangles, G. Balavoine and A. Loffet, Tetrahedron Lett., 1989, 30, 2641;
52. (b) O. Dangles, F. Guibé, G. Balavoine, S. Lavielle and A. Marquet, J. Org. Chem., 1987, 52, 4984.
53. F. Rabanal, E. Giralt and F. Albericio, Tetrahedron, 1995, 51, 1449.
54. M. S. Shekhani, G. Grübler, H. Echner and W. Voelter, Tetrahedron Lett., 1990, 31, 339.
55. For an application of TBAF to cleave benzyl ester from Pam resins, see: M. Ueki, K. Kai, M. Amemiya, H. Horino and H. Oyamada, J. Chem. Soc. Chem. Commun., 1988, 414.
56. For an application of TBAF to cleave phenacyl ester resin, see: Y. Kiso, T. Kimura, Y. Fujiwara, M. Shimokura and A. Nishitani, Chem. Pharm. Bull., 1988, 36, 5024.
57. For cleavage of silicon-oxygen bond from resin, see: (a) D. G. Mullen and G. Barany, Tetrahedron Lett., 1987, 28, 491;
58. (b) R. Ramage, C. A. Barron, S. Bielecki and D. W. Thomas, Tetrahedron Lett., 1987, 28, 4105.
59. r strategy for solid-phase synthesis of C-terminal peptide acids, see: H. G. Chao, M. S. Bernatowicz, P. D. Reiss, C. E. Klimas and G. R. Matsueda, J. Am. Chem. Soc., 1994, 116, 1746.
60. K. Akaji, M. Yoshida, T. Tatsumi, Y. Fujiwara and Y. Kiso, J. Chem. Soc., Chem. Commun., 1990, 288.
61. (a) D. H. Rich and S. K. Gurwara, J. Am. Chem. Soc., 1975, 97, 1575.
62. For a recent development of a new ortho-nitrobenzyl photolabile linker for solid-phase synthesis, see: C. P. Holmes and D. G. Jones, J. Org. Chem., 1995, 60, 2318.
63. R. Bollhagen, M. Schmiedberger, K. Barlos and E. Grell, J. Chem. Soc., Chem. Commun., 1994, 2559.
64. M. Nomizu, Y. Inagaki, T. Yamashita, A. Ohkubo, A. Otaka, N. Fujii, P. P. Roller and H. Yajima, Int. J. Peptide Protein Res., 1991, 37, 145.
65. For an excellent coverage of these topics, see: ref. 21a.
66. M. Frankel, D. Gertner, D. Wagner and A. Zilka, J. Org. Chem., 1965, 30, 1596.
67. S. T. Vijayarachavan and T. R. Balasubramanian, J. Organomet. Chem., 1985, 282, 17.
68. M. Gonzalez Sierra, O. A. Mascaretti, V. M. Merkuza, E. L. Tosti and E. A. Ruveda, Phytochemistry, 1974, 13, 2865.
69. O. A. Mascaretti, V. M. Merkuza, G. E. Ferraro, E. A. Ruveda, C. J. Chang and E. Wenkert, Phytochemistry, 1972, 11, 1133.
70. A. Bodanszky, M. Bodanszky, N. Chandramouli, J. Z. Kwei, J. Martinez and J. C. Tolle, J. Org. Chem., 1980, 45, 72.
71. Vogel's Textbook of Practical Organic Chemistry, 5th edn., Longman Scientific & Technical: Essex, New York, 1989.