Lanthionine macrocyclization by in situ activation of serine

Journal of Peptide Research

Volumn 51, Issue 6, 1998, Pages 432-436

  Mayer, John P ^a   Zhang, Jingwen ^a   Groeger, Stefan ^a   Liu, Chuan Fa ^a   Jarosinski, Mark A ^a  

^a AMGEN INC   (United States)

Author keywords

Cyclic peptides; Lanthionine; Macrocyclization; Solid phase; Thioether formation

Indexed keywords

CYCLOPEPTIDE; LANTHIONINE; SERINE; SULFIDE;

ARTICLE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN ASSEMBLY; PROTEIN CONFORMATION;

EID: 0031801016     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1998.tb00641.x     Document Type: Article

References (27)

1. Hruby, V.J. (1982) Life Sci. 31, 189-199
2. Hruby, V.J. Al-Obeidi, F. & Kazmierski, W. (1990) Biochem. J. 268, 249-262
3. Rizo, J. & Gierasch, L. (1992) Annu. Rev. Biochem. 61, 387-418
4. Moroder, L., Besse, D., Musiol, H.-J., Bohner, S.R. & Siedler, F. (1996) Biopolymers (Pep. Sci.) 40, 207-234
5. Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M. & Barany, G. (1994) in Methods in Molecular Biology Peptide Synthesis Protocols, (Pennington, M.W., Dunn, B.M., eds.), vol. 35: pp. 91-169, Humana Press, Totowa, NJ
6. Rudinger, J. & Jost, K. (1964) Experientia 20, 570-571
7. Jost, K., Prochazka, Z., Cort, J.H., Skopkova, J., Prusik, Z. & Sorm, F. (1974) Collect. Czech. Chem. Commun. 39, 2835-2856
8. Prochazka, Z. & Jost, K. (1980) Collect. Czech. Chem. Commun. 45, 1305-1316
9. Gasson, M.J. (1995) in Genetics and Biochemistry of Antibiotic Production (Vining, L.C., Stuttard, C., eds.), pp. 283-306. Butterworth-Heinemann, Newton, MA
10. Sahl, H.-G., Jack, R.W. & Bierbaum, G. (1995) Eur. J. Biochem. 230, 827-853
11. Jack, R.W. & Sahl, H.-G. (1995) Trends Biotechnol. 13, 269-278
12. Jung, G. & Sahl, H.-G., eds. (1988) Nisin and Novel Lantibiotics, ESCOM Science, Leiden, The Netherlands
13. Wakimiya, T., Ueki, Y., Shiba, T., Kido, Y. & Motoki, Y. (1985) Tetrahedron Lett. 26, 665-668
14. Polinsky, A., Cooney M.G., Toy-Palmer, A., Osapay, G. & Goodman, M. (1992) J. Med. Chem. 35, 4185-4194
15. Wang, S.H.H., Bahmanyar, S., Taulane, J.P. & Goodman, M. (1996) in Peptides: Chemistry Structure and Biology (Kaumaya, P.T.P., Hodges, R.S., eds.), pp. 715-716, Mayflower Scientific LTD, Cornwall, England, UK
16. Osapay, G., Prokai, L., Kim, H.-S., Medzihradszky, K.F., Coy, D.H., Liapakis, G., Reisine, T., Melacini, G., Zhu, Q., Wang, S.H.-H., Mattern, R.-H. & Goodman, M. (1997) J. Med. Chem. 40, 2241-2251
17. Melacini, G., Zhu, Q., Osapay, G. & Goodman, M. (1997) J. Med. Chem. 40, 2252-2258
18. Fukase, K., Kitazawa, M., Sano, A., Shimbo, K., Horimoto, S., Fujita, H., Kubo, A., Wakamiya, T. & Shiba, T. (1992) Bull. Chem. Soc. Jpn. 65, 2227-2240
19. Harpp, D.N. & Gleason, J.G. (1971) J. Org. Chem. 36, 73-80
20. Goodman, M. & Shao, H. (1996) Pure Appl. Chem. 68, 1303-1308
21. Osapay, G. & Goodman, M. (1993) J. Chem. Soc. Chem. Commun. 1599-1600
22. Mayer, J.P., Heil, J.R., Zhang, J. & Munson, M.C. (1995) Tetrahedron Lett. 36, 7387-7390
23. Rink, H. (1987) Tetrahedron Lett. 28, 3787-3790
24. Hughes, D.L. (1992) in Organic Reactions (Paquette, L.A., ed.), vol. 42, pp. 335-656, John Wiley & Sons, New York, NY
25. Valerio, R.M., Bray, A.M. & Patsiouras, H. (1996) Tetrahedron Lett. 37, 3019-3022
26. Ellman, G.L. (1959) Arch. Biochem. Biophys. 82, 70-73
27. Hayashi, H., Nakanishi, K., Brandon, C. & Marmur, J. (1973) J. Am. Chem. Soc. 95, 8749-8757