Brevetoxin
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Brevetoxin (PbTx), or brevetoxins, are a suite of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis. Brevetoxins are neurotoxins that bind to voltage-gated sodium channels in nerve cells, leading to disruption of normal neurological processes and causing the illness clinically described as neurotoxic shellfish poisoning (NSP).[1]
Although brevetoxins are most well-studied in K. brevis, they are also found in other species of Karenia and at least one large fish kill has been traced to brevetoxins in Chattonella.[1]
Brevetoxin A | Brevetoxin B | |
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chemical structure | ||
subtypes |
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Other Brevetoxins:
- Brevetoxin-5 (PbTx-5): like PbTx-3, but acetylated hydroxyl group in position 38.
- Brevetoxin-6 (PbTx-6): like PbTx-2, but double bond 27-28 is epoxidated.
Brevetoxin-2 was synthesized in 1995 by K. C. Nicolaou and coworkers in 123 steps with 91% average yield (final yield ~9·10-6).[2]
References
- ^ a b Watkins, Sm; Reich, A; Fleming, Le; Hammond, R (2008), "Neurotoxic shellfish poisoning" (Free full text), Marine drugs 6 (3): 431–55, doi: , PMID 19005578, PMC 2579735, http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=19005578
- ^ Microsoft PowerPoint - brevetoxin synthesis
See also
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