Convenient one-pot synthesis of cystine-containing peptides using the trimethylsilyl chloride-dimethyl sulfoxide/trifluoroacetic acid system and its application to the synthesis of bifunctional anti-HIV compounds

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1998, Pages 495-500

  Tamamura, Hirokazu ^a   Ishihara, Tsunehito ^a   Oyake, Hirorni ^a   Imai, Makoto ^a   Otaka, Akira ^a   Ibuka, Toshiro ^a   Arakaki, Rieko ^b   Nakashima, Hideki ^b   Murakami, Tsutomu ^c   Waki, Michinori ^d   Matsumoto, Akiyoshi ^d   Yamamoto, Naoki ^c   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KAGOSHIMA UNIVERSITY   (Japan)

^c TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^d SEIKAGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748636950     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706545k     Document Type: Article

References (23)

1. Preliminary communication: H. Tamamura, T. Ishihara, A. Otaka, T. Koide, K. Miyoshi, T. Ibuka and N. Fujii, J. Chem. Soc., Perkin Trans. 1, 1996, 1911.
2. See, for example: H. Tamamura, R. Ikoma, M. Niwa, S. Funakoshi, T. Murakami and N. Fujii, Chem. Pharm. Bull, 1993, 41, 978;
3. H. Tamamura, T. Murakami, M. Masuda, A. Otaka, W. Takada, T. Ibuka, H. Nakashima, M. Waki, A. Matsumoto, N. Yamamoto and N. Fujii, Biochem. Biophys. Res. Commun., 1994, 205, 1729.
4. N. Fujii, A. Otaka, A. Okamachi, T. Watanabe, H. Arai, H. Tamamura, S. Funakoshi and H. Yajima in Peplides 1988, ed. G. Jung and E. Bayer, Walter de Gruyter, Berlin, 1988, p. 58;
5. J. P. Tam, C-R. Wu, W. Liu and J.-W. Zhang, J. Am. Chem. Soc., 1991, 113, 6657;
6. A. Otaka, T. Koide, A. Shide and N. Fujii, Tetrahedron Lett., 1991, 32, 1223.
7. H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda, T. Ibuka and N. Fujii, Int. J. Pept. Protein Res., 1995, 45, 312.
8. (a) K. Akaji, T. Tatsumi, M. Yoshida, T. Kimura, Y. Fujiwara and Y. Kiso, J. Am. Chem. Soc., 1992, 114, 4137;
9. (b) T. Koide, A. Otaka, H. Suzuki and N. Fujii, Synlett, 1991, 345.
10. D. F. Veber, J. D. Milkowski, S. L. Varga, R. G. Denkewaler and R. Hirschmann, J. Am. Chem. Soc., 1972, 94, 5456.
11. S. S. Wang, J. Am. Chem. Soc., 1973, 95, 1328.
12. H. Rink, Tetrahedron Lett., 1987, 28, 3787.
13. A. Dryland and R. C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1986, 125.
14. N. Fujii, A. Otaka, N. Sugiyama, M. Hatano and H. Yajima, Chem. Pharm. Bull., 1987, 35, 3880.
15. S. Kumagaye, H. Kuroda, K. Nakajima, T. Watanabe, T. Kimura, T. Masaki and S. Sakakibara, Int. J. Pept. Protein Res., 1988, 32, 519.
16. H. Nakashima, M. Masuda, T. Murakami, Y. Koyanagi, A. Matsumoto, N. Fujii and N. Yamamoto, Antimicrob. Agents Chemother., 1992, 36, 1249.
17. H. Tamamura, T. Ishihara, A. Otaka, T. Murakami, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto and N. Fujii, Biochim. Biophys. Acta, 1996, 1298, 37 (and references therein).
18. H. Mitsuya, J. Clin. Exp. Med. (Tokyo), 1996, 176, 108.
19. R. Pauwels, B. M. Balzarini, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter and E. De Clercq, J. Virol. Methods, 1988, 20, 309.
20. S. Shibahara, S. Mukai, H. Morisawa, H. Nakashima, S. Kobayashi and N. Yamamoto, Nucleic Acids Res., 1989, 17, 239.
21. J. P. Tam, Proc. Natl Acad. Sci. USA, 1988, 85, 5409.
22. S. Funakoshi, H. Tamamura, N. Fujii, K. Yoshizawa, H. Yajima, K. Miyasaka, A. Funakoshi, M. Ohta, Y. Inagaki and L. A. Carpino, J. Chem. Soc., Chem. Commun., 1988, 1589.
23. For a previous synthesis of compound 4, see B. M. Tadayoni, B. M. Friden, L. R. Walus and G. F. Musso, Bioconjugate Chem., 1993, 4, 139.