Beta -Carbolines, biogenetically readily derivable from tryptophan, are a familiar structural feature of marine alkaloids. Conversely, alpha -carbolines, also derivable from tryptophan, are rare. The grossularines, isolated from a tunicate, constitute the only previous example. We now report the structure of a cyclic hexapeptide with a tryptophan-derived alpha -carboline which is part of a fused tetracyclic system that also includes phenylalanine-derived (Phe-2) imidazolone.
This document is the accepted manuscript version of a published work that appeared in final form in Journal of the American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ja00136a026. This article may be cited as: Nakao, Y., Yeung, B. K. S., Yoshida, W. Y., Scheuer, P. J., & Kelly-Borges, M. (1995). Kapakahine B, a cyclic hexapeptide with an alpha-carboline ring system from the marine sponge Cribrochalina olemda. Journal of the American Chemical Society, 117(31), 8271-8272. doi:10.1021/ja00136a026
Florida Atlantic University. Harbor Branch Oceanographic Institute contribution #1103.