Relationship between the cyclization and conformation of pentapeptide active esters related to gramicidin S having no protecting group on the side chain of the ornithine residue

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 4, 1997, Pages 899-904

  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

CYCLOPEPTIDE; GRAMICIDIN S;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE;

EID: 0030998921     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.899     Document Type: Article

References (17)

1. A. R. Battershy and L. C. Craig, J. Am. Chem. Soc., 73, 1887 (1951).
2. 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-IBU Commission of Biological Nomenclature.
3. R. Schwyzer and P. Sieber, Helv. Chem. Acta., 411, 2186 (1958).
4. a) N. Izumiya, T. Kato, T. 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), pp. 15-47;
5. b) K. Sato, R. Kato, and U. Nagai, Bull. Chem. Soc. Jpn., 64, 256 (1991);
6. c) S. Imazu, Y. Shimohigashi, H. Kodama, K. Sakaguchi, M. Waki, T. Kato, and N. Izumiya, Int. Pept. Protein Res., 32, 298 (1988);
7. d) M. Tamaki and S. Akabori, Bull. Chem. Soc. Jpn., 64, 2563 (1991);
8. e) M. Tamaki, S. Akabori, and I. Muramatu, Bull. Chem. Soc. Jpn., 66, 3113 (1993).
9. M. Tamaki, S. Akabori, and I. Muramatsu, J. Am. Chem. Soc., 115, 10492 (1993).
10. S. G. Laland, Φ. Frøyshov, C. Gilhuus-Moe, and T. L. Zimmer. Nature New Biol., 239, 43 (1972).
11. a) M. Tamaki, T. Okitsu, M. Araki, H. Sakamoto, M. Takimoto, and I. Muramatsu, Bull. Chem. Soc. Jpn., 58, 531 (1985);
12. b) M. Tamaki, M. Takimoto, M. Hayashi, and I. Muramatsu, Bull. Chem. Soc. Jpn., 62, 594 (1989).
13. The analytical data for [D-Val]-semi-GS was shown in Table 1. [D-Val)-semi-GS showed no activity against Staphylococcus aureus ATCC 6583, Streptomyces pyogenes N.Y.5, Corynebaclerium diphtheriae P.W.8, Micrococcus pyogenes ATCC 10240, Bacillus subtillis ATCC6633, Escherichia coli NIHJ-JC2, and Proteus vulgaris OX 19.
14. The upper limit of concentration for the CD studies approaches to that used in the NMR experiments, so the observations made in the two experiments can be correlated.
15. H. Sakamoto, K. Tanimura, Y. Shimohigashi, M. Waki, K. Kawano, and M. Ohno, "Peptide Chemistry 1991," ed by A. Suzuki, Protein Research Foundation, Osaka (1992), pp. 425-430.
16. I. D. Rae and H. A. Scheraga, Biochem. Biophys. Res. Commun., 81, 481 (1978).
17. S. F. Brady, S. L. Varga, R. M. Freidinger, D. A. Schwenk, M. Mendlowski, F. W. Holly, and D. F. Veber, J. Org. Chem., 44, 3101 (1979).