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Brevetoxin
From Wikipedia, the free encyclopedia
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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[2] | Brevetoxin B[3] | |
|---|---|---|
| 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-B was synthesized in 1995 by K. C. Nicolaou and coworkers in 123 steps with 91% average yield (final yield ~9·10−6).[4] and in 2004 a total of 90 steps with an average 93% yield for each step (0.14% overall).[3]
K. C. Nicolaou and coworkers reported their synthesis of Brevetoxin-1 in 1998.[5] In 2009, Michael Crimmins and co-workers reported their synthesis of Brevetoxin-1 as well.[6]
Biosynthesis
A proposed biosynthetic route includes a novel polyketide formation involving Claisen condensation of a dicarboxylic acid with the alpha-position of the second carboxylic function with a loss of a carboxyl group.[7]
References
- ^ a b Watkins SM, Reich A, Fleming LE, Hammond R (2008). "Neurotoxic Shellfish Poisoning". Marine Drugs 6 (3): 431–455. DOI:10.3390/md20080021. PMC 2579735. PMID 19005578. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2579735.
- ^ Nicolaou KC, Yang Z, Shi G, Gunzner JL, Agrios KA, Gärtner P (1998). "Total Synthesis of Brevetoxin A". Nature 392 (6673): 264–269. DOI:10.1038/32623. PMID 9521320.
- ^ a b Matsuo G, Kawamura K, Hori N, Matsukura H, Nakata T (2004). "Total Synthesis of Brevetoxin-B" (pdf). Journal of the American Chemical Society 126 (44): 14374–14376. DOI:10.1021/ja0449269. http://www.chem.queensu.ca/courses/09/CHEM223/Handouts/BrevetoxinSynthesis.pdf.
- ^ Nicolaou KC, Rutjes FP, Theodorakis EA, Tiebes J, Sato M, Untersteller E (1995). "Total Synthesis of Brevetoxin B. 3. Final Strategy and Completion". Journal of the American Chemical Society 117 (41): 10252–10263. DOI:10.1021/ja00146a010.
- ^ Nicolaou KC, Yang Z, Shi GQ, Gunzner JL, Agrios KA, Gärtner P (1998). "Total Synthesis of Brevetoxin A". Nature 392 (6673): 264–269. DOI:10.1038/32623.
- ^ Crimmins MT, Zuccarello JL, Ellis JM, McDougall PJ, Haile PA, Parrish JD, Emmitte KA (2009). "Total Synthesis of Brevetoxin A". Organic Letters 11 (2): 489–492. DOI:10.1021/ol802710u.
- ^ Chou HN, Shimizu Y (1987). "Biosynthesis of Brevetoxins. Evidence for the Mixed Origin of the Backbone Carbon Chain and the Possible Involvement of Dicarboxylic Acids". Journal of the American Chemical Society 109 (7): 2184–2185. DOI:10.1021/ja00241a048.
See also
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