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Lyngbyatoxin-a
Chemical compound From Wikipedia, the free encyclopedia
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Lyngbyatoxin-a is a type of alkaloid cyanotoxin produced by certain cyanobacteria species, most notably Moorea producens (formerly classified as Lyngbya majuscula). It is produced as defense mechanism to ward off any would-be predators of the bacterium, being a potent blister agent as well as carcinogen. Low concentrations cause a common skin condition known as seaweed dermatitis.[1][2][3][4][5][6]
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Biosynthesis

Lyngbyatoxin is a terpenoid indole alkaloid hybrid that belongs to the class of non-ribosomal peptides (NRPs).[7] Lyngbyatoxin contains a nucleophilic indole ring that takes part in the activation of protein kinases. Figure 1, shows the biosynthesis of Lyngbyatoxin reported by Neilan et al. and Gerwick et al. The non-ribosomal peptide synthase (NRPS) LtxA protein condenses L-methyl-valine and L-tryptophan to form the linear dipeptide N-methyl-L-valyl-L-tryptophan. The latter is released via a NADPH-dependent reductive cleavage to form the aldehyde which is subsequently reduced to the corresponding alcohol. A P450-dependent monooxygenase called LtxB then performs the oxidation and subsequent cyclization of N-methyl-L-valyl-L-tryptophan. Finally, LtxC transfers a geranyl functional group from geranyl pyrophosphate (GPP) to carbon number 7 of the indole ring.
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References
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