Biomimetic synthesis of a peptide antibiotic, gratisin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 14, 1997, Pages 2045-2050

  Tamaki, Makoto ^a   Komiya, Seiji ^a   Akabori, Sadatoshi ^a   Muramatsu, Ichiro ^b  

^a TOHO UNIVERSITY   (Japan)

^b Tokyo Bunka Junior College   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748963629     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701537b     Document Type: Article

References (23)

1. C. F. Gause and M. G. Brazhnikov, Am. Rev. Sov. Med., 1944, 2, 134;
2. D. C. Hodgkin and B. M. Oughton, Biochem. J., 1957, 65, 752;
3. S. Nozaki and I. Muramatsu, J. Antibiot., 1984, 37, 689;
4. Bull. Chem. Soc. Jpn., 1985, 58, 331.
5. Amino acid residues with no prefix have the L-configuration. The abbreviations for amino acids and peptides are in accordance with the rules of the IUPAC-IUB Commission on Biological Nomenclature.
6. N. Izumiya, T. Kato, H. Aoyagi, M. Waki and M. Kondo, Synthetic Aspects of Biologically Active Cyclic Peptides-Gramicidin S and Tyrocidines, Kodansha, Tokyo and Halsted Press, New York, 1979, p. 49;
7. M. Tamaki, M. Takimoto, M. Hayashi and I. Muramatsu, Bull. Chem. Soc. Jpn., 1989, 62, 594;
8. M. Tamaki, S. Akabori and I. Muramatsu, Bull. Chem. Soc. Jpn., 1993, 66, 3113;
9. Y. Minematsu, M. Waki, K. Suwa, T. Kato and N. Izumiya, Tetrahedron Lett., 1980, 21, 2179.
10. S. G. Laland, Ph. Frøyshov, C. Gilhuus-Moe and T. L. Zimmer, Nature (London) New Biol., 1972, 239, 43.
11. M. Tamaki, S. Akabori and I. Muramatsu, J. Am. Chem. Soc., 1993, 115, 10 492.
12. G. G. Zharikova, S. P. Myaskovskaya and A. B. Silaev, Vestn. Mosk. Univ. Ser. Biol. Pochvoved. Geol. Geogr., 1972, 27, 110
13. (Chem. Abstr., 1972, 77, 162982p);
14. S. P. Myaskovskaya, G. G. Zharikova and A. B. Silaev, Vestn. Mosk. Univ. Ser. Biol. Pochvoved. Geol. Geogr., 1973, 28, 123
15. (Chem. Abstr., 1974, 80, 37446c);
16. G. G. Zharikova, A. P. Zarubina, D. M Kherat, S. P. Myaskovskaya and V. N. Maksimov, Antibiot. IKh Prod., 1975, 163
17. (Chem. Abstr., 1976, 84, 119884r).
18. M. Tamaki, Bull. Chem. Soc. Jpn., 1984, 57, 3210;
19. M. Tamaki, M. Takimoto and I. Muramatsu, Bull. Chem. Soc. Jpn., 1987, 60, 2101.
20. The cyclic monomers produced by the cyclization of the linear hexapeptide active esters 1 and 3-6 were found to have no antibiotic activity. On the other hand, H-Orn-Leu-D-Phe-Pro-D-Tyr-Val, isolated from a reaction mixture of peptide 2, showed the activities 1/4-1/8 of that of GR against Bacillus subtilis ATCC 6633, Streptomyces pyogenes N.Y.5, Staphylococcus aureus MS353 and Micrococcus luteus ATCC 9341.
21. M. Tamaki, S. Komiya, S. Akabori and I. Muramatsu, Bull. Chem. Soc. Jpn., 1997, 70, 899.
22. H. Kleinkauf and H. von Dohren, Eur. J. Biochem., 1990, 192, 1.
23. M. Tamaki, S. Akabori and I. Muramatsu, Bull. Chem. Soc. Jpn., 1991, 64, 583.