Decarbamoylsaxitoxin
 Structure of dcSTX
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IUPAC name
(3aS,4R,10aS)-2,6-diamino-4-(hydroxymethyl)-3a,4,8,9-tetrahydro-3H-pyrrolo[1,2-c]purine-10,10-diol
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3D model (JSmol)
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| C9H16N6O3 | |||
| Molar mass | 256.26 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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Decarbamoylsaxitoxin, abbreviated as dcSTX, is a neurotoxin which is naturally produced in dinoflagellate. DcSTX is one
of the many analogues of saxitoxin (STX). Saxitoxin, as shown in figure 1, is a tricyclic alkaloid compound, which has multiple structural related neurotoxins. One of those related neurotoxins is neosaxitoxin (NSTX) in which the nitrogen at place 2 is not bound to a hydrogen, but to a hydroxyl group. Another toxic analogue of saxitoxin is gonyautoxin (GTX). The difference between GTX and STX is that on the carbon at place 11, a hydrogensulfate is bound.
Between dcSTX, NSTX and GTX, dcSTX is the one which varies most from saxitoxin. In dcSTX there is a double bond between carbon 2 and 3, while there is a single bond in STX. This also results in that the double bound N to carbon number 3 in STX, is a single bound NH2 in dcSTX. Another difference between decarbamoylsaxitoxin and saxitoxin is that the amino-carbonyl-oxy-methyl group at place 1 in STX, is only a CH2OH group in dcSTX.
Even though there are slight differences between all saxitoxin related compounds, all those saxitoxins are neurotoxins which have an impact on the sodium channels. When in contact with one of the saxitoxins it can cause a severe illness, which is known as paralytic shellfish poisoning (PSP).
From eating shellfish, under which mussels, clams, whelks and scallops, multiple illnesses can result. One of them is sensory and motor paralysis, known as paralytic shellfish poisoning (PSP), which results from ingestion of saxitoxin and its derivatives, such as decarbamoylsaxitoxin. Shellfish can concentrate a dinoflagellate known as Gonyaulax tamarensis, which elaborates saxitoxin. Mussels are known to filter up to 20 litres of water a day, which is why they are very likely to carry the toxin when the surrounding water is contaminated. This dinoflagellate does not affect the shellfish, but when an organism eats the scallop shuckings, it risks getting poisoned.
Synonyms of decarbamoylsaxitoxin are; dcSTX-saxitoxin, decarbamoylsaxitoxin, decarbamylsaxitoxin
Decarbamoylsaxitocin is like saxitoxin a very hygroscopic solid. Since saxitoxins and its derivatives are mainly produced by the Gonyaulax tamarensis dinoflagellate, for a long time the exact synthesis pathway was unknown. Saxitoxin was the first paralytic shellfish toxin from which the total synthesis was described. This was done by Kishi and his research group in 1977. In 1991 they managed to describe the synthesis of decarbamoylsaxitoxin as well.
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