Synthesis of [Hexafluorovalyl1,1′]gramicidin S

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 5, 1996, Pages 1383-1389

  Arai, Toru ^a   Imachi, Takashi ^a   Kato, Tamaki ^a   Ogawa, H Iyehara ^a   Fujimoto, Tsutomu ^a   Nishino, Norikazu ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GRAMICIDIN DERIVATIVE; GRAMICIDIN S; GRAMICIDIN S [1,1' HEXAFLUOROVAZLINE]; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; MEMBRANE PERMEABILITY; NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS;

EID: 0029949348     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1383     Document Type: Article

References (37)

1. For recent review, see: V. P. Kukhar', J. Fluorine Chem., 69, 199 (1994); "Fluorine-containing Amino Acids; Synthesis and Properties," ed by V. P. Kukhar' and V. A. Soloshonok, John Wiley & Sons, Chichester (1995).
2. For recent review, see: V. P. Kukhar', J. Fluorine Chem., 69, 199 (1994); "Fluorine-containing Amino Acids; Synthesis and Properties," ed by V. P. Kukhar' and V. A. Soloshonok, John Wiley & Sons, Chichester (1995).
3. M. R. C. Gerstenberger and A. Hass, Angew. Chem., Int. Ed. Engl., 20, 647 (1981); B. Badet, D. Roice, and C. T. Walsh, Biochemistry, 23, 5188 (1984); M. H. Gelb, J. P. Svaren, and R. H. Abeles, Biochemistry; 24, 1813 (1985).
4. M. R. C. Gerstenberger and A. Hass, Angew. Chem., Int. Ed. Engl., 20, 647 (1981); B. Badet, D. Roice, and C. T. Walsh, Biochemistry, 23, 5188 (1984); M. H. Gelb, J. P. Svaren, and R. H. Abeles, Biochemistry; 24, 1813 (1985).
5. M. R. C. Gerstenberger and A. Hass, Angew. Chem., Int. Ed. Engl., 20, 647 (1981); B. Badet, D. Roice, and C. T. Walsh, Biochemistry, 23, 5188 (1984); M. H. Gelb, J. P. Svaren, and R. H. Abeles, Biochemistry; 24, 1813 (1985).
6. T. Watanabe, A. Yamatodani, K. Maeyama, and H. Wada, Trends Pharmacol. Sci., 11, 363 (1990); R. B. Silverman and S. M. Nanavati, J. Med. Chem., 33, 931 (1990).
7. T. Watanabe, A. Yamatodani, K. Maeyama, and H. Wada, Trends Pharmacol. Sci., 11, 363 (1990); R. B. Silverman and S. M. Nanavati, J. Med. Chem., 33, 931 (1990).
8. a) W. H. Vine, K.-h. Hsieh, and G. R. Marshall, J. Med. Chem., 24, 1043 (1981)
9. b) K.-h. Hsieh, P. Needleman, and G. R. Marshall, J. Med. Chem., 30, 1097 (1987).
10. I. Ojima, K. Kato, K. Nakahashi, T. Fuchigami, and M. Fujita, J. Org. Chem., 54, 4511 (1989); I. Ojima, K. Kato, F. A. Jameison, J. Conway, K. Nakahashi, M. Hagiwara, T. Miyamae, and H. E. Radunz, Bioorg. Med. Chem. Lett., 2, 219 (1992).
11. I. Ojima, K. Kato, K. Nakahashi, T. Fuchigami, and M. Fujita, J. Org. Chem., 54, 4511 (1989); I. Ojima, K. Kato, F. A. Jameison, J. Conway, K. Nakahashi, M. Hagiwara, T. Miyamae, and H. E. Radunz, Bioorg. Med. Chem. Lett., 2, 219 (1992).
12. T. Tsushima, K. Kawada, S. Ishihara, N. Uchida, O. Shiratori, J. Higaki, and M. Hirata, Tetrahedron, 44, 5375 (1988).
13. H. Tanaka, F. Osakada, S.-i. Ohashi, M. Shiraki, and E. Munekata, Chem. Lett., 1986, 391; A. P. Campbell, J. Cachia, and B.D. Sykes, Biochem. Cell Biol., 69, 674 (1991); J. T. Gerig, Prog. NMR Spectrosc., 26, 293 (1994).
14. H. Tanaka, F. Osakada, S.-i. Ohashi, M. Shiraki, and E. Munekata, Chem. Lett., 1986, 391; A. P. Campbell, J. Cachia, and B.D. Sykes, Biochem. Cell Biol., 69, 674 (1991); J. T. Gerig, Prog. NMR Spectrosc., 26, 293 (1994).
15. H. Tanaka, F. Osakada, S.-i. Ohashi, M. Shiraki, and E. Munekata, Chem. Lett., 1986, 391; A. P. Campbell, J. Cachia, and B.D. Sykes, Biochem. Cell Biol., 69, 674 (1991); J. T. Gerig, Prog. NMR Spectrosc., 26, 293 (1994).
16. N. Nishino and H. Mihara, in "New Functionality Materials, Volume B Synthesis and Function Control of Biofunctionality Materials," ed by T. Tsuruta, M. Doyama, M. Seno, and Y. Imanishi, Elsevier Science Publishers B. V., Amsterdam (1993), pp. 147-152; S. F. Bets, D. P. Raleigh, and W. F. DeGrado, Curr. Opin. Struct. Biol., 3, 501 (1993); J. P. Schneider and J. W. Kelly, Chem. Rev., 95, 2169 (1995).
17. N. Nishino and H. Mihara, in "New Functionality Materials, Volume B Synthesis and Function Control of Biofunctionality Materials," ed by T. Tsuruta, M. Doyama, M. Seno, and Y. Imanishi, Elsevier Science Publishers B. V., Amsterdam (1993), pp. 147-152; S. F. Bets, D. P. Raleigh, and W. F. DeGrado, Curr. Opin. Struct. Biol., 3, 501 (1993); J. P. Schneider and J. W. Kelly, Chem. Rev., 95, 2169 (1995).
18. N. Nishino and H. Mihara, in "New Functionality Materials, Volume B Synthesis and Function Control of Biofunctionality Materials," ed by T. Tsuruta, M. Doyama, M. Seno, and Y. Imanishi, Elsevier Science Publishers B. V., Amsterdam (1993), pp. 147-152; S. F. Bets, D. P. Raleigh, and W. F. DeGrado, Curr. Opin. Struct. Biol., 3, 501 (1993); J. P. Schneider and J. W. Kelly, Chem. Rev., 95, 2169 (1995).
19. Abbreviations used are according to IUPAC-IUB Commissions, Eur. J. Biochem., 138, 9 (1984). Other abbreviations: GS, gramicidin S; Hfv. 4,4,4,4′, 4′, 4′-hexafluoro-L-valine; Boc. t-butoxycarbonyl ; Z, benzyloxycarbonyl ; BOP, benzotriazol-l-yloxytris (diethylamino)phosphonium hexafluorophosphate; DCC, dicyclohexylcarbodiimide; HOBt, 1-hydroxybenzotriazole; DMF, N,N-dimethylformamide; DMSO, dimethyl sulfoxide; TFA, trifluoro-acetic acid; DIEA, N,N-diisopropylethylamine; CF, 5(6)-carboxyfluorescein; HEPES, 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid; CD, circular dichroism.
20. N. Izumiya, Y. Kato, H. Aoyagi, M. Waki, and M. Kondo, "Synthetic Aspects of Biologically Active Cyclic Peptides-Gramicidin S and Tyrocidins," Kodansha, Tokyo (1979); G. Némethy and H. A. Sheraga, Biochem. Biophys. Res. Commun., 118, 643 (1984).
21. N. Izumiya, Y. Kato, H. Aoyagi, M. Waki, and M. Kondo, "Synthetic Aspects of Biologically Active Cyclic Peptides-Gramicidin S and Tyrocidins," Kodansha, Tokyo (1979); G. Némethy and H. A. Sheraga, Biochem. Biophys. Res. Commun., 118, 643 (1984).
22. E. Kaiser, R. L. Colescott, C. D. Bossinger, and P. I. Cook, Anal. Biochem., 34, 595 (1970).
23. C. Danzin, P. Bey, D. Schirlin, and N. Claveric, Biochem. Pharmacol., 31, 387 (1982).
24. a) G. Ösapay, A. Profit, and J. W. Taylor, Tetrahedron Lett., 31, 6121 (1990)
25. b) M. Xu, N. Nishino, H. Mihara, T. Fujimoto, and N. Izumiya, Chem. Lett., 1992, 191
26. c) N. Nishino, M. Xu, H. Mihara, and T. Fujimoto, Bull. Chem. Soc. Jpn., 65, 991 (1992)
27. d) N. Nishino, T. Arai, J. Hayashida, H. I. Ogawa, H. Yamamoto, and S. Yoshikawa, Chem. Lett., 1994, 2435.
28. T. Higashijima, T. Miyazawa, M. Kawai, and U. Nagai, Biopolymers, 25, 2295 (1986); A. C. Bach, II. C. J. Eyermann, J. D. Gross, M. J. Bower, R. L. Harlow, P. C. Weber, and W. F. DeGrado, J. Am. Chem. Soc., 116, 3207 (1994).
29. T. Higashijima, T. Miyazawa, M. Kawai, and U. Nagai, Biopolymers, 25, 2295 (1986); A. C. Bach, II. C. J. Eyermann, J. D. Gross, M. J. Bower, R. L. Harlow, P. C. Weber, and W. F. DeGrado, J. Am. Chem. Soc., 116, 3207 (1994).
30. K. Wüthrich, "NMR of Proteins and Nucleic Acids," John Wiley & Sons, N. Y. (1986).
31. H. Mihara, T. Kanmera, M. Toshida, S. Lee, H. Aoyagi, T. Kato, and N. Izumiya, Bull. Chem. Soc. Jpn., 60, 697 (1987); H. Mihara, N. Nishino, H. I. Ogawa, N. Izumiya, and T. Fujimoto, Bull. Chem. Soc. Jpn., 65, 228 (1992); S. Ando, H. Nishikawa, H. Takiguchi, S. Lee, and G. Sugihara, Biochim. Biophys. Acta, 1147, 42 (1993).
32. H. Mihara, T. Kanmera, M. Toshida, S. Lee, H. Aoyagi, T. Kato, and N. Izumiya, Bull. Chem. Soc. Jpn., 60, 697 (1987); H. Mihara, N. Nishino, H. I. Ogawa, N. Izumiya, and T. Fujimoto, Bull. Chem. Soc. Jpn., 65, 228 (1992); S. Ando, H. Nishikawa, H. Takiguchi, S. Lee, and G. Sugihara, Biochim. Biophys. Acta, 1147, 42 (1993).
33. H. Mihara, T. Kanmera, M. Toshida, S. Lee, H. Aoyagi, T. Kato, and N. Izumiya, Bull. Chem. Soc. Jpn., 60, 697 (1987); H. Mihara, N. Nishino, H. I. Ogawa, N. Izumiya, and T. Fujimoto, Bull. Chem. Soc. Jpn., 65, 228 (1992); S. Ando, H. Nishikawa, H. Takiguchi, S. Lee, and G. Sugihara, Biochim. Biophys. Acta, 1147, 42 (1993).
34. N. Otsuji, T. Higashi, and J. Kawamata, Biken J., 15, 49 (1972).
35. Jpn. Patent JP59-157045 (1984).
36. B. F. Gisin, Anal. Chim. Acta, 58, 248 (1972).
37. A. Tani, S. Lee, O. Oishi, H. Aoyagi, and M. Ono, J. Biochem., 117, 560 (1995).