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Brevetoxin B

Researchers have achieved the first total synthesis of brevetoxin B, a marine neurotoxin associated with "red tides," such as the one that some believe to have occurred when Moses visited afflictions upon the Egyptians.

Brevetoxin B is a neurotoxin produced by algae called Ptychodiscus brevis Davis or Gymnodinium breve Davis. The algae proliferate during red tide incidents, vast phytoplankton blooms that actually turn the sea red, brown, or green. The compound and related toxins are believed to have been responsible for massive fish kills from red tides in several regions of the world and poi sonings of humans who ate affected seafood. For example, 14 humpback whales died and many people were sickened by a red tide incident in 1987 in Cape Cod Bay, Mass. Brevetoxin B exerts its neurotoxic ef fects by binding to sodium charmels on nerve and muscle cell membranes, causing an excessive influx of sodium ions across the membranes, which leads to cell death.


Please go back and get the <a href="../quicktime/">plug-in</a> for Netscape Brevetoxin B has now been synthesized after a 12-year effort by chemistry Professor K. C. Nicolaou and coworkers at Scripps Research Institute, La Jol la, Calif., and the University of California, San Diego J Am. Chem. Soc. , 117, 1171 and 1173 (1995)]. The compound has a complex structure that includes 11 trans-fused rings and 23 stereocenters. Nicolaou and co workers synthesized it from the simple starting material 2-deoxy-ribose in 83 steps. The overall yield of the synthesis was 0.043%, but the average yield for each site was about 91%.