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

Research output: Contribution to journal › Article

71 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Cyclic Peptides
Stereochemistry
Amides
Tryptophan
Spectrum analysis
Nitrogen
Carbon
Degradation
Peptides
indole

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

The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda. / Yeung, B. K S; Nakao, Youichi; Kinnel, R. B.; Carney, J. R.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M.

In: Journal of Organic Chemistry, Vol. 61, No. 20, 1996, p. 7168-7173.

Research output: Contribution to journal › Article

Yeung, BKS, Nakao, Y, Kinnel, RB, Carney, JR, Yoshida, WY, Scheuer, PJ & Kelly-Borges, M 1996, 'The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda', Journal of Organic Chemistry, vol. 61, no. 20, pp. 7168-7173. https://doi.org/10.1021/jo960725e
Yeung BKS, Nakao Y, Kinnel RB, Carney JR, Yoshida WY, Scheuer PJ et al. The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda. Journal of Organic Chemistry. 1996;61(20):7168-7173. https://doi.org/10.1021/jo960725e
Yeung, B. K S ; Nakao, Youichi ; Kinnel, R. B. ; Carney, J. R. ; Yoshida, W. Y. ; Scheuer, P. J. ; Kelly-Borges, M. / The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda. In: Journal of Organic Chemistry. 1996 ; Vol. 61, No. 20. pp. 7168-7173.
@article{a526c921c34348dc8d37e5c96e19c495,
title = "The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda",
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 Youichi Nakao and Kinnel, {R. B.} and Carney, {J. R.} and Yoshida, {W. Y.} and Scheuer, {P. J.} and M. Kelly-Borges",
year = "1996",
doi = "10.1021/jo960725e",
language = "English",
volume = "61",
pages = "7168--7173",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

AU - Yeung, B. K S

AU - Nakao, Youichi

AU - Kinnel, R. B.

AU - Carney, J. R.

AU - Yoshida, W. Y.

AU - Scheuer, P. J.

AU - Kelly-Borges, M.

PY - 1996

Y1 - 1996

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.

UR - http://www.scopus.com/inward/record.url?scp=0029805586&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029805586&partnerID=8YFLogxK

U2 - 10.1021/jo960725e

DO - 10.1021/jo960725e

M3 - Article

AN - SCOPUS:0029805586

VL - 61

SP - 7168

EP - 7173

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -

Access to Document