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.
This document is the accepted manuscript version of a published work that appeared in final form in Journal of Organic Chemistry after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo960725e. This article may be cited as: Young, B. K. S., Nakao, Y., Kinnel, R. B., Carney, J. R., Yoshida, W. Y., & Scheuer, P. J. (1996). The Kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda. Journal of Organic Chemistry, 61(20), 7168-7173. doi:10.1021/jo960725e
Florida Atlantic University. Harbor Branch Oceanographic Institute contribution #1163.