Palau'amine is a toxic alkaloid compound synthesized naturally by Stylotella agminata, a species of sea sponge found in the southwest Pacific Ocean. The name of the molecule derives from the island nation of Palau, near which the sponges are found.
The substance was first isolated and described in 1993.[1] Containing nine nitrogen atoms, the molecule is considered highly complex. The precise atomic structure was pinned down in 2007,[2] and two years later the molecule was synthesized in the lab by a team at the Scripps Research Institute in La Jolla, California.[3][4]
Biosynthesis
A pathway to this dimeric pyrrole-imidazole alkaloid has been hypothesized to include a key oxidation of a β-ketoester with Mn(OAc)3 initiated a cascade radical cyclization sequence to deliver an ageliferin skeleton.[5]
References
- ↑ Robin B. Kinnel, Henning Peter Gehrken,, Paul J. Scheuer: Palau'amine: a cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata. In: Journal of the American Chemical Society. 115. Jahrgang, Nr. 8, 1993, S. 3376–3377, doi:10.1021/ja00061a065.
- ↑ Bethany Halford: Sponge Alkaloids: Palau'amine Reconsidered. In: Chemical & Engineering News. 85. Jahrgang, Nr. 10, 2007, S. 12, doi:10.1021/cen-v085n010.p012a (acs.org).
- ↑ Ian B. Seiple, Shun Su, Ian S. Young, Chad A. Lewis, Junichiro Yamaguchi, Phil S. Baran: Total Synthesis of Palauamine. In: Angewandte Chemie International Edition. 49. Jahrgang, 2010, S. 1095, doi:10.1002/anie.200907112.
- ↑ Alexis Madrigal: Bizarre Sea Sponge Compound Finally Synthesized by Humans. 14. Januar 2010, abgerufen am 15. Januar 2010.
- ↑ Ma Z, Lu J, Wang X, Chen C: Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine. In: Chem Commun (Camb). 47. Jahrgang, Nr. 1, 7. Januar 2011, S. 427–9, doi:10.1039/c0cc02214d, PMC 2999656 (freier Volltext).