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

doi:10.1021/jo960725e

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

^*Corresponding author for this work

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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 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo960725e

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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.",

author = "Yeung, {B. K.S.} and Y. Nakao and Kinnel, {R. B.} and Carney, {J. R.} and Yoshida, {W. Y.} and Scheuer, {P. J.} and M. Kelly-Borges",

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AU - Yeung, B. K.S.

AU - Nakao, Y.

AU - Kinnel, R. B.

AU - Carney, J. R.

AU - Yoshida, W. Y.

AU - Scheuer, P. J.

AU - Kelly-Borges, M.

PY - 1996/1/1

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N2 - 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.

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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The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

Abstract

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