Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1997, Pages 1501-1510

  Bitan, Gal ^a   Muller, Dan ^a   Kasher, Ron ^a   Gluhov, Evgenia V ^a   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748737482     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a608389g     Document Type: Article

References (26)

1. Part 3, D. Muller, I. Zeltser, G. Bitan and C. Gilon, J. Org. Chem., 1997, 62, 411.
2. C. Gilon, D. Halle, M. Chorev, Z. Selinger and G. Byk, Biopolymers, 1991, 31, 745.
3. C. Gilon, I. Zeltser, V. Rashti-Behar, D. Muller, G. Bitan, D. Halle, G. Bar-Akiva, Z. Selinger and G. Byk, in Peptide Chemistry 1992, ed. N. Yanaihara, ESCOM, Leiden, 1993, pp. 482-485.
4. Y. Ovchinnikov, G. Chipens and V. Ivanov, in Peptides 1982, Walter de Gruyter, Berlin, 1983, pp. 1-18.
5. C. Gilon, D. Halle, M. Chorev, Z. Selinger and G. Byk, in Peptides Chemistry and Biology, ESCOM, Leiden, 1992, pp. 476-477.
6. S. Reissmann, G. Greiner, J. Jezek, C. Amberg, B. Müller, L. Seyfarth, L. F. P. De Castro and I. Paegelow, Biomed. Pept. Proteins Nucleic Acids, 1995, 1, 51.
7. G. Byk and C. Gilon, J. Org. Chem., 1992, 57, 5687.
8. G. Bitan and C. Gilon, Tetrahedron, 1995, 51, 10 513.
9. R. W. Feenstra, E. H. M. Stokkingreef, R. J. F. Nivard and H. C. J. Ottenheijm, Tetrahedron, 1988, 44, 5583.
10. H. Wurziger, Kontakte (Darmstadt), 1987, 8.
11. J. A. Fehrentz and B. Castro, Synthesis, 1983, 676.
12. D. Julie, M. Mayer, P. Schmitt, G. Drapeau, D. Regoli and R. Mickelot, Eur. J. Med. Chem., 1991, 26, 921.
13. M. Rodriguez, A. Heitz and J. Matinez, Int. J. Pept. Protein Res., 1992, 39, 273.
14. T. Shimizu, R. Kobayashi, H. Ohmori and T. Nakata, Synlett, 1995, 650.
15. M. Kolb, J. Barth, J. G. Heydt and M. J. Jung, J. Med Chem., 1987, 30, 267.
16. J. L. Herrmann, G. R. Kieczykowski, R. F. Romanet, P. J. Wepplo and R. H. Schlessinger, Tetrahedron Lett., 1973, 4711.
17. Y. Ohfune, N. Kurokawa, N. Higuchi, M. Saito, M. Hashimoto and T. Tanaka, Chem. Lett., 1984, 87, 441.
18. D. R. Bolin, I. Sytwu, F. Humiec and J. Meienhofer, Int. J. Pept. Protein Res., 1989, 33, 353.
19. G. Byk, PhD. thesis submitted to the senate of The Hebrew University of Jerusalem, 1990.
20. R. J. Simon, R. S. Kania, R. N. Zuckermann, V. D. Huebner, D. A. Jewell, S. Banville, S. Ng, L. Wang, S. Rosenberg, C. K. Marlowe, D. C. Spellmeyer, R. Tan, A. D. Frankel, D. V. Santi, F. E. Cohen and P. A. Bartlett, Proc. Natl. Acad. Sci. USA, 1992, 89, 9367.
21. P. C. Andrews, D. M. Leonard, W. L. Cody and T. K. Sawyer, in Methods in Molecular Biology, ed. B. M. Dunn and M. W. Pennington, Humana Press, Totowa, 1994, vol. 36.
22. J. E. Rivier, J.-C. Jiang, L. Simo, S. C. Koerber, J. Porter, A. G. Craig and C. A. Hoeger, in Peptides: Chemistry, Structure and Biology, ed. P. T. P. Kaumaya and R. S. Hodges, Mayflower Scientific Ltd, Kingswinford (UK), 1996, pp. 275-277.
23. E. L. Eliel and S. Morris-Natschke, J. Am. Chem. Soc., 1984, 106, 2937.
24. D. J. Ramón and M. Yus, J. Org. Chem., 1991, 56, 3825.
25. F. Foubelo, F. Lloret and M. Yus, Tetrahedron, 1993, 49, 8465.
26. M. Bodanszky and A. Bodanszky, The Practice of Peptide Synthesis, Springer-Verlag, Berlin, 1984, p. 20.