The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

B. K.S. Yeung, Y. Nakao, R. B. Kinnel, J. R. Carney, W. Y. Yoshida, P. J. Scheuer, M. Kelly-Borges

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Abstract

Four cyclic peptides, kapakahines A-D, were isolated from the marine sponge Cribrochalina olemda. Their structures including complete stereochemistry were elucidated by spectral analysis and chemical degradation. The unique structural feature of these peptides is the lack of an amide linkage between two tryptophan residues. Instead the ring is closed by a bond from the indole nitrogen of Trp-1 to the β-carbon of Trp-2.

Original languageEnglish
Pages (from-to)7168-7173
Number of pages6
JournalJournal of Organic Chemistry
Volume61
Issue number20
DOIs
Publication statusPublished - 1996 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Yeung, B. K. S., Nakao, Y., Kinnel, R. B., Carney, J. R., Yoshida, W. Y., Scheuer, P. J., & Kelly-Borges, M. (1996). The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda. Journal of Organic Chemistry, 61(20), 7168-7173. https://doi.org/10.1021/jo960725e