Gonyautoxin
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IUPAC name
(3aS,4R,9R,10aS)-2,6-Diamino-4-(((aminocarbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-1H,10H-pyrrolo(1,2-c)purine-9,10,10-triol 9-(Hydrogen Sulfate)
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| Other names
Gonyautoxin 2, GTX-2, GTX-II
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PubChem CID
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| Properties | |
| C10H17N7O8S | |
| Molar mass | 395.35 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gonyautoxins (GTX) are a few similar toxic molecules that are naturally produced by algae. They are part of the group of saxitoxins, a large group of neurotoxins along with a molecule that is also referred to as saxitoxin (STX), neosaxitoxin (NSTX) and decarbamoylsaxitoxin (dcSTX). Currently eight molecules are assigned to the group of gonyautoxins, known as gonyautoxin 1 (GTX-1) to gonyautoxin 8 (GTX-8). Ingestion of gonyautoxins through consumption of mollusks contaminated by toxic algae can cause a human illness called paralytic shellfish poisoning (PSP).
Gonyautoxins are naturally produced by several marine dinoflagellates species (Alexandrium sp., Gonyaulax sp., Protogonyaulax sp.). The paralytic shellfish poisoning caused by these toxins is connected with dinoflagellate blooms known as “red tides”, even though the coloration of the water isn’t a necessity. The threshold concentration of the organisms that are capable to produce the toxins is lower than the lowest visually detectable concentration. Subsequently the toxins are taken up by shellfish and undergo bioaccumulation.
As part of the group of satoxins, the gonyautoxins have their structure based on the 2,6-diamino-4-methyl-pyrollo[1,2-c]-purin-10-ol skeleton (also known as the Saxitoxin-gonyautoxin skeleton). The different molecules only differ from each other by their substituents, some of them only by a mere stereoisomerism such as GTX-2 and GTX-3. Gonyautoxins are detectable by means of High Performance Liquid Chromatography (HPLC), which has been tested on mice., In 2009 a monoclonal antibody is developed to detect gonyautoxin 2 or 3 in aquatic products. The detection limit is measured to be lower than 0.74 micrograms per milliliter.
While the gonyautoxins are naturally available, a synthesis procedure of some of them is known as well. Gonyautoxin 2 can for example be synthesized from L-serine methyl ester, via gonyautoxin 3. In this process firstly the L-serine methyl ester is treated with aldehyde, so that it can react to close the ring structure. The formed allyl is deprotected by the addition of [[SO3CH2CCl3]]. Subsequently a RH-catalyzed amination reaction with guanidine is followed, forming the tricyclic frame of GTX-3. The relatively unstable intermediates of several reactions in this process are modified by using three protecting groups. Removing these groups gives 11β-hydrosaxitoxin as a product, which will then be sulfated on the C 11-alcohol. GTX-2 is formed by incubating the product in an aequeous solution at pH 8, in order to make the epimerization at C11 still occur.
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