View PDF Version
 
DOI: 10.1039/A706545K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 495-500

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[hair space]1

(Note: The full text of this document is currently only available in the PDF Version )

Hirokazu Tamamura, Tsunehito Ishihara, Hiromi Oyake, Makoto Imai, Akira Otaka, Toshiro Ibuka, Rieko Arakaki, Hideki Nakashima, Tsutomu Murakami, Michinori Waki, Akiyoshi Matsumoto, Naoki Yamamoto and Nobutaka Fujii

Abstract

A one-pot synthesis of cystine-containing peptides is achieved by treatment of protected peptidyl resins with trimethylsilyl chloride–dimethyl sulfoxide/trifluoroacetic acid in the presence of anisole. This methodology has been successfully applied to the synthesis of highly active anti-HIV peptides conjugated with 3′-azido-3′-deoxythymidine.

References

  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 Search PubMed.
  2. See, for example: H. Tamamura, R. Ikoma, M. Niwa, S. Funakoshi, T. Murakami and N. Fujii, Chem. Pharm. Bull., 1993, 41, 978 Search PubMed; 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 CAS.
  3. N. Fujii, A. Otaka, A. Okamachi, T. Watanabe, H. Arai, H. Tamamura, S. Funakoshi and H. Yajima, in Peptides 1988, ed. G. Jung and E. Bayer, Walter de Gruyter, Berlin, 1988, p. 58 Search PubMed; J. P. Tam, C.-R. Wu, W. Liu and J.-W. Zhang, J. Am. Chem. Soc., 1991, 113, 6657 Search PubMed; A. Otaka, T. Koide, A. Shide and N. Fujii, Tetrahedron Lett., 1991, 32, 1223 CrossRef CAS.
  4. 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 Search PubMed.
  5. (a) K. Akaji, T. Tatsumi, M. Yoshida, T. Kimura, Y. Fujiwara and Y. Kiso, J. Am. Chem. Soc., 1992, 114, 4137 CrossRef CAS; (b) T. Koide, A. Otaka, H. Suzuki and N. Fujii, Synlett, 1991, 345 CAS.
  6. D. F. Veber, J. D. Milkowski, S. L. Varga, R. G. Denkewaler and R. Hirschmann, J. Am. Chem. Soc., 1972, 94, 5456 CrossRef CAS.
  7. S. S. Wang, J. Am. Chem. Soc., 1973, 95, 1328 CrossRef CAS.
  8. H. Rink, Tetrahedron Lett., 1987, 28, 3787 CrossRef CAS.
  9. A. Dryland and R. C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1986, 125 RSC.
  10. N. Fujii, A. Otaka, N. Sugiyama, M. Hatano and H. Yajima, Chem. Pharm. Bull., 1987, 35, 3880 CAS.
  11. S. Kumagaye, H. Kuroda, K. Nakajima, T. Watanabe, T. Kimura, T. Masaki and S. Sakakibara, Int. J. Pept. Protein Res., 1988, 32, 519 Search PubMed.
  12. H. Nakashima, M. Masuda, T. Murakami, Y. Koyanagi, A. Matsumoto, N. Fujii and N. Yamamoto, Antimicrob. Agents Chemother., 1992, 36, 1249 CAS.
  13. 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 CrossRef CAS (and references therein).
  14. H. Mitsuya, J. Clin. Exp. Med. (Tokyo), 1996, 176, 108 Search PubMed.
  15. R. Pauwels, B. M. Balzarini, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter and E. De Clercq, J. Virol. Methods, 1988, 20, 309 CrossRef CAS.
  16. S. Shibahara, S. Mukai, H. Morisawa, H. Nakashima, S. Kobayashi and N. Yamamoto, Nucleic Acids Res., 1989, 17, 239 CAS.
  17. J. P. Tam, Proc. Natl. Acad. Sci. USA, 1988, 85, 5409 CAS.
  18. 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 Search PubMed.
  19. 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 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.