Protection of cysteine in Fmoc solid phase peptide synthesis (SPPS): New variations of classical theme

Chimica Oggi

Volumn 21, Issue 6, 2003, Pages 22-25

  Mizhiritskii, Michael ^a   Shpernat, Yacov ^a   Askinazi, Boris ^a  

^a ArtChem Division   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

9 FLUORENYLMETHYLCARBONYLCYSTEINAMINE; 9 FLUORENYLMETHYLOXYCARBONYLCYSTEINAMIDE; CYSTEINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; DEPROTECTION REACTION; PEPTIDE SYNTHESIS; PROTEIN ANALYSIS; REVIEW;

EID: 0041730309     PISSN: 0392839X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (51)

1. L. Moroder, D. Besse, H.-J. Musiol, S. Rudolph-Bohner, F. Siedler; Biopolymers 40 207 (1996)
2. NovaBioChem Catalog, Synthesis Note Index, 2002/3, p. 4.4-4.5
3. F. Cavelier, J. Daunis, R. Jaquier; Bull. Soc. Chim. Fr. 2 210 (1990)
4. M. Frankel, D. Genther, H. Jacobson, A. Zilkha; J. Chem. Soc. 1390 (1960)
5. (a) I. Photaki, e.a.; J. Chem. Soc. (C) 2683 (1970)
6. (b) R.G. Hiskey, B.J. Adams; J. Org. Chem. 30 1340 (1965)
7. D.F. Veber, e.a.; J. Am. Chem. Soc. 94 5456 (1972)
8. J.J. Pastuszak, A. Chimiak; J. Org. Chem. 46 1868 (1981)
9. Y. Kiso, e.a; Tetrahedron Lett. 30 1979 (1989)
10. M.C. Munson, C. Garcia-Echeverria, F. Albericio, G. Barany; Pept.: Chem. Biol., Proc. Am. Pept. Symp., 12th (1992), Meeting Date 1991, 605-6; J. Org. Chem. 57 3013 (1992)
11. M.C. Munson, C. Garcia-Echeverria, F. Albericio, G. Barany; Pept.: Chem. Biol., Proc. Am. Pept. Symp., 12th (1992), Meeting Date 1991, 605-6; J. Org. Chem. 57 3013 (1992)
12. D. Denis, E. Trifiliff; J. Peptide Sci. 6 372 (2000)
13. E. Atherton, M. Pinori, R.C. Sheppard R; J. Chem. Soc., Perkin I. 2057 (1985)
14. W.F. Heath, J.P. Tam, R.B. Merrifield; Int. J. Pept. Protein Res. 28 498 (1986)
15. R.W. Hanson, H.D. Law; J. Chem. Soc. 7285 (1965)
16. P.K. Chakravarty, R.K. Olsen; J. Org. Chem. 43 1270 (1978)
17. O. Nishimura, C. Kitada, M. Fujino; Chem. Pharm. Bull. 26 1576 (1978)
18. M. Bodanszky, M.A. Bednarek; Int. J. Pept. Protein Res. 20 434 (1982)
19. P.J.E. Brownlee, e.a.; J. Chem. Soc. 3832 (1964)
20. A. Otaka, e.a.; Chem. Pharm. Bull. 37 526 (1989)
21. B.H. Rietman, R.F.R. Peters, G.I. Tesser; Recl. Trav. Chim. Pays-Bas. 114 1 (1995)
22. S.J. Stewart, C.N.C. Drey; J. Chem. Soc., Perkin I. 1753 (1990)
23. A. Schroll, G. Barany; J. Org. Chem. 54 244 (1989)
24. K. Nokihara, H. Berndt; J. Org. Chem. 43 4893 (1978)
25. M. Ueki, K. Shinozaki; Bull. Chem. Soc., Jpn. 56 1187 (1983)
26. S. Ideka, e.a.; Bull. Chem. Soc., Jpn. 52 1431 (1979)
27. L. Horner, H. Lindel; Phosphorus Sulfur 15 1 (1983)
28. O. Garcia, E. Nicolas, F. Albericio; Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids. Collected Papers, International Symposium, 6th, York, United Kingdom, Aug. 31-Sept. 4, 1999 (2001), Meeting Date 1999, p. 289-290
29. L. Bland, R., Ramage; Ibid., p. 247-248
30. M. Royo, J. Alsina, E. Giralt, U. Slomczynska, F. Albericio; Pept.: Chem., Struct. Biol., Proc. Am. Pept. Symp., 13th (1994), Meeting Date 1993, 116-18
31. M. Royo et al.; Innovation Perspect. Solid Phase Synth. Collect. Pap., Int. Symp., 2nd (1992), Meeting Date 1991, p. 461-5
32. F. Brtnik, M. Krojidlo, T. Barth, K. Jost; Collection of Czech. Chem. Commun. 46 286 (1981)
33. Y. Han, G. Barany; J. Org. Chem. 62 3841 (1997)
34. C. W. West, M. A. Estiarte, D.H. Rich; Org. Lett. 3 1205 (2001)
35. A.M. Kimbonguila, A. Merzouk, F. Guibe, A. Loffet; Tetrahedron 55 6931 (1999)
36. P. Gomez-Martinez, A.M. Kimbonguila, F. Guibe; Tetrahedron 55 6945 (1999)
37. M. Ueki, e.a.; Synthesis 21 (1993)
38. R. Eritja, J.-P. Ziehler-Martin, P.A. Walker, T.D. Lee, K. Legesse, F. Albericio, B.E. Kaplan; Tetrahedron 43 2675 (1987)
39. Huang H., Carey R.I., Int. J. Pept. Protein Res. 48 290 (1997)
40. B.H. Rietman, R.F.R. Peters, G.I. Tesser; Synth. Commun. 24 1323 (1994)
41. Will be published soon.
42. M.S. Bernatowicz, R. Matsueda, G.R. Matsueda; Int. J. Pept. Protein Res. 28 107 (1986)
43. B. Ponsati, E. Giralt, D. Andreu; Tetrahedron 46 8255 (1990)
44. E.E. Buellesbach, C. Schwabe; J. Biol. Chem. 266 10764 (1991)
45. R.G. Simmonds, D.E. Tupper. J.R. Harris; Int. J. Pept. Protein Res. 43 363 (1994)
46. B. Sacca, D. Barth, H.-J. Musiol, L. Moroder; J. Peptide Sci. 8 205 (2002)
47. S. Zuberi, A. Glen, R.C. Hider, S.S. Bansal; Tetrahedron Lett. 39 7567 (1998)
48. O. Ploux, G. Chassaing, A. Marquet; Int. J. Pept. Protein Res. 29 162 (1987)
49. F. Albericio, e.a.; Int. J. Pept. Protein Res. 34 124 (1989)
50. G. Mezo, N. Mihala, D. Andreu, F. Hudecz; Bioconjugate Chem. 11 484 (2000)
51. G. Mourier, e.a.; J. Immunol. Methods 171 65 (1994)