New chlorinated peptides from the tropical marine sponge Dysidea sp.

Tetrahedron

Volumn 57, Issue 21, 2001, Pages 4603-4607

  Stapleton, Bronwin L ^a   Cameron, George M ^a   Garson, Mary J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Chlorinated peptide; DIBAH; NaBH4; NMR; Sponges

Indexed keywords

ALCOHOL; BUTYRIC ACID DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHLORINATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PRIORITY JOURNAL; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 0035927212     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00379-9     Document Type: Article

References (28)

1. Cameron G.M., Stapleton B.L., Simonsen S.M., Brecknell D.D., Garson M.J. Tetrahedron. 56:2000;5247.
2. Kazlauskas R., Lidgard R.O., Wells R.J., Vetter W. Tetrahedron Lett. 1977;3183. Dysidenin/isodysidenin series:
3. Charles C., Braekman J.C., Daloze D., Tursch B., Karlsson R. Tetrahedron Lett. 1978;1519.
4. Charles C., Braekman J.C., Daloze D., Tursch B. Tetrahedron. 36:1980;2133.
5. Erickson K.L., Wells R.J. Aust. J. Chem. 35:1982;31.
6. Biskupiak J.E., Ireland C.M. Tetrahedron Lett. 25:1984;2935.
7. de Laszlo S.E., Williard P.G. J. Am. Chem. Soc. 107:1985;199.
8. Braekman J.C., Daloze D., Deneubourg F., Lippert E., Van Sande J. New J. Chem. 14:1990;705.
9. Dumdei E.J., Simpson J.S., Garson M.J., Byriel K.S., Kennard C.H.L. Aust. J. Chem. 50:1997;139.
10. Dumrongchai N., Ponglimanont C., Stapleton B.L., Garson M.J. ACGC Chem. Res. Comm. 2001;. in press.
11. Kazlauskas R., Murphy P.T., Wells R.J. Tetrahedron Lett. 1978;4945. Diketopiperazines.
12. Su J.Y., Zhong Y.L., Zeng L.M., Shen W., Wang Q.W. Chin. Chem. Lett. 4:1993;139.
13. Su J.-Y., Zhong Y.-L., Zeng L.-M., Wei S., Wang Q.-W., Mak T.C.W., Zhou Z.-Y. J. Nat. Prod. 56:1993;637.
14. Fu X., Zeng L.-M., Su J.-Y., Pais M. J. Nat. Prod. 60:1997;695.
15. Fu X., Ferreira M.L.G., Schmitz F.J., Kelly-Borges M. J. Nat. Prod. 61:1998;1226.
16. Hofheinz W., Oberhänsli W.E. Helv. Chim. Acta. 60:1977;660. Pyrrolidinones.
17. Köhler H., Gerlach H. Helv. Chim. Acta. 67:1984;1783.
18. Gebreyesus T., Yosief T., Carmely S., Kashman Y. Tetrahedron Lett. 29:1988;3863.
19. Carmely S., Gebreyesus T., Kashman Y., Skelton B.W., White A.H., Yosief T. Aust. J. Chem. 43:1990;1881.
20. Isaacs S., Berman R., Kashman Y., Gebreyesus T., Osief T. J. Nat. Prod. 54:1991;83.
21. Lee G.M., Molinski T.F. Tetrahedron Lett. 33:1992;7671.
22. Other peptides: (b) Unson M.D., Rose C.B., Faulkner D.J., Brinen L.S., Steiner J.S., Clardy J. J. Org. Chem. 58:1993;6336.
23. Clark W.D., Crews P. Tetrahedron Lett. 36:1995;1185.
24. MacMillan J.B., Molinski T.F. J. Nat. Prod. 63:2000;155.
25. Trousdale E.K., Taylor S.W., Parkin S., Hope H., Molinski T.F. Nat. Prod. Lett. 12:1998;61.
26. Helmchen G., Wegner G. Tetrahedron Lett. 26:1985;6047.
27. We are grateful to Professor J. C. Braekman, Brussels, for providing this information.
28. Revised proton assignments by DQFCOSY analysis.