Efficient, non-acidolytic method for the selective cleavage of N-Boc amino acid and peptide phenacyl esters linked to a polystyrene resin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 2, 1998, Pages 355-358

  Furlán, Ricardo L E ^a   Mata, Ernesto G ^a   Mascaretti, Oreste A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748631301     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704118g     Document Type: Article

References (46)

1. For recent reviews, see: M. Schelhaas and H. Waldmann, Angew. Chem., Int. Ed. Engl., 1996, 35, 2056;
2. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991;
3. P. J. Kocienski, Protecting Groups, Georg Thieme Verlag, Stuttgart, 1994;
4. K. Jarowicki and P. Kocienski, Contemp. Org. Synth., 1995, 2, 315;
5. K. Jarowicki and P. Kocienski, Contemp. Org. Synth., 1996, 3, 397.
6. For a recent review of the chemical deprotection of ester functional groups, see: C. J. Salomon, E. G. Mata and O. A. Mascaretti, Tetrahedron, 1993, 49, 3691.
7. For a recent representative method of deprotection of Pac esters, see: R. N. Ram and L. Singh, Tetrahedron Lett., 1995, 36, 5401.
8. Two excellent reviews of organic synthesis on solid supports have recently appeared, providing a comprehensive account of solid-phase synthesis of small molecules, as well as of oligomers; see: J. S. Früchel and G. Jung, Angew. Chem., Int. Ed. Engl., 1996, 35, 17;
9. P. H. H. Hermkens, H. C. J. Ottenheijm and D. Rees, Tetrahedron, 1996, 52, 4527.
10. B. Ruhland, A. Bhandari, E. M. Gordon and M. A. Gallop, J. Am. Chem.Soc., 1996, 118, 253.
11. For a recent review of combinatorial synthesis, see: N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 51, 8135.
12. For a recent special issue on combinatorial chemistry applied to drug synthesis, see: Acc. Chem. Res., 1996, 29, 111.
13. For leading references on the applications of combinatorial chemistry to drug discovery, see: M. A. Gallop, R. W. Barret, W. J. Dower, S. P. A. Fodor and E. M. Gordon, J. Med. Chem., 1994, 37, 1233;
14. E. W. Gordon, R. W. Barret, W. J. Dower, S. P. A. Fodor and M. A. Gallop, J. Med. Chem., 1994, 37, 1385.
15. For recent reviews on synthesis and applications of small-molecule libraries, see: F. Balkenhohl, C. von dem. Bussche-Hünnefeld, A. Lansky and C. Zechel, Angew. Chem. Int. Ed. Engl., 1996, 35, 2388;
16. L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555.
17. R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
18. S. S. Wang, J. Am. Chem. Soc., 1973, 95, 1328;
19. J. Org. Chem., 1975, 40, 1235;
20. J. K. Chang, M. Shimizu and S. S. Wang, J. Org. Chem., 1976, 41, 3255.
21. A. R. Mitchell, B. W. Erickson, M. N. Ryabtsev, R. S. Hodges and R. B. Merrifield, J. Am. Chem. Soc., 1976, 98, 7357;
22. 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.
23. M. Mergler, R. Tanner, J. Gostelli and P. Grogg, Tetrahedron Lett., 1988, 29, 4005;
24. M. Mergler, R. Nyfeler, R. Tanner, J. Gostelli and P. Grogg, Tetrahedron Lett., 1988, 29, 4009.
25. B. Riniker, A. Flörsheimer, H. Fretz, P. Sieber and B. Kamber, Tetrahedron, 1993, 49, 9307.
26. T. Miziguchi, K. Shigezane and N. Takamura, Chem. Pharm. Bull., 1970, 18, 1465.
27. G. Barany and R. B. Merrifield, in The Peptides. Analysis, Synthesis and Biology, ed. E. Gross and J. Meienhofer, Academic Press, New York, 1980, vol. 2, p. 1.
28. For the cleavage of Boc-peptide benzyl esters linked to polystyrene resins by HF/p-cresol or p-thiocresol and its application in combinatorial chemical synthesis, see: B. Déprez, X. Williard, L. Bourel, H. Coste, F. Hyafil and A. Tartar, J. Ant. Chem. Soc., 1995, 117, 5405.
29. For a recent review of TFA cleavage/deprotection in N-Fmoc/O-tert-BU ether peptide benzyl esters linked to Wang and Sasrin resins, see: F. Dick, in Peptide Synthesis Protocols, ed. M. W. Pennington and B. M. Duran, Humana Press, Totowa, New Jersey, 1994, p. 63.
30. 2, see ref. 4.
31. 2, see: I. Dalcol, F. Rabanal, M. D. Ludevid, F. Albericio and E. Giralt, J. Org. Chem., 1995, 60, 7575.
32. For the cleavage of Boc-peptide phenacyl esters, linked to a polystyrene-DVB resin, by fluoride ion, see: Y. Kiso, T. Kimura, Y. Fujiwara, M. Shimokura and A. Nishitani, Chem. Pharm. Bull., 1988, 36, 5024;
33. Y. Kiso, T. Kimura, Y. Fujiwara. H. Sakikawa and K. Akaji, Chem. Pharm. Bull., 1990, 38, 270.
34. The naming of organotin compounds follows the trivial system using 'tin' as a suffix, as in ref. 22a.
35. (a) C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Org. Chem., 1994, 59, 7259.
36. For preliminary communications see (b) E. G. Mata and O. A. Mascaretti, Tetrahedron Lett., 1988, 29, 6893;
37. C. J. Salomon, E. G. Mata and O. A. Mascaretti; (c) Tetrahedron Lett., 1991, 32, 4239;
38. (d) J. Chem. Soc., Perkin Trans. 1, 1996, 995.
39. R. L. E. Furlán, E. G. Mata and O. A. Mascaretti, Tetrahedron Lett., 1996, 37, 5229.
40. Polystyrene 3% DVB resin (Bio-Beads S-X3) was purchased from Bio-Rad.
41. J. M. Stewart and J. D. Young, Solid Phase Peptide Synthesis, Freeman, San Francisco, 1969, p. 113.
42. Abbreviations used in this paper for amino acids and for the designation of peptides follow the rules of the IUPAC-IUBC Commission of Biochemical Nomenclature in J. Biol. Chem., 1972, 247, 977. Other abbreviations are as follows: Bn, benzyl; Boc, tert-butoxycarbonyl; DVB, divinylbenzene.
43. 1H NMR spectra were identical with those reported by P. B. Simons and W. A. Graham, J. Organomet. Chem., 1967, 8, 479.
44. For recent reviews on convergent solid-phase peptide synthesis, see: P. L. Williams, F. Albericio and E. Giralt, Tetrahedron, 1993, 49, 11 065;
45. H. Benz, Synthesis, 1994, 337.
46. D-Values for compounds 2, 4, 6 and 8 were taken from the Analytical Data Sheet from Bachem Feinchemikalien AG (Switzerland).