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Brevetoxin

Introduction

Brevetoxin, 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).

Brevetoxin A Brevetoxin B
chemical structure
Brevetoxin A
Brevetoxin A
Brevetoxin B
Brevetoxin B
subtypes
  • Brevetoxin-1 (PbTx-1) R = -CH2C(=CH2)CHO
  • Brevetoxin-7 (PbTx-7) R = -CH2C(=CH2)CH2OH
  • Brevetoxin-10 (PbTx-10) R = -CH2CH(-CH3)CH2OH
  • Brevetoxin-2 (PbTx-2) R = -CH2C(=CH2)CHO
  • Brevetoxin-3 (PbTx-3) R = -CH2C(=CH2)CH2OH
  • Brevetoxin-8 (PbTx-8) R = -CH2COCH2Cl
  • Brevetoxin-9 (PbTx-9) R = -CH2CH(CH3)CH2OH

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. Nicolau and coworkers in 123 steps with 91% average yield (final yield ~9·10-6).[1]

References

References

  1. ↑ http://www.chemistry.msu.edu/courses/cem852/classics/Chapter37.pdf
See also

See also

de:Brevetoxine