The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

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

doi:10.1021/jo960725e

The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

B. K S Yeung, Youichi 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 language	English
Pages (from-to)	7168-7173
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	61
Issue number	20
DOIs	https://doi.org/10.1021/jo960725e
Publication status	Published - 1996
Externally published	Yes

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ASJC Scopus subject areas

Organic Chemistry

Cite this

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

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AU - Yoshida, W. Y.

AU - Scheuer, P. J.

AU - Kelly-Borges, M.

PY - 1996

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AB - 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.

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10.1021/jo960725e