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Synthesis of Saxitoxin and Its Derivatives

Organic Letters, 2020
The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid.
Yuya Okuyama   +5 more
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Structure of saxitoxin

Journal of the American Chemical Society, 1975
Saxitoxin is a neurotoxin found in various molluscs. The p-bromobenzenesulfonate-saxitoxin was crystallized and the structure was determined by single-crystal x-ray diffraction. Bond distances and angles were discussed, and a computer generated drawing of the final x-ray model was presented. (DDA)
E. J. Schantz   +6 more
openaire   +1 more source

Saxitoxin

The surface waters contaminated with cyanobacteria, which are utilized for drinking, irrigation, and recreational purposes, poses a potential hazard to population health, as well as domestic animals and wildlife. Due to the observed trends of rising temperatures and the increased levels of nutrient pollution in surface waters, the occurrence of marine ...
Senanur Ozsoy   +2 more
openaire   +2 more sources

Derivatives of saxitoxin

Bioorganic Chemistry, 1981
Abstract The preparation, spectral characterization, chromatographic and biological properties of several derivatives of saxitoxin, a highly potent neurotoxin, are described. Derivatives include decarbamoylsaxitoxin, both epimers of dihydrosaxitoxin (α- and β-saxitoxinol) and both epimers of decarbamoylsaxitoxinol, as well as several isotopically ...
Frank E. Koehn   +4 more
openaire   +1 more source

First report of saxitoxin in octopi

Toxicon, 2004
We report for the first time, the presence of saxitoxin (STX) in a common cephalopod, Octopus (Abdopus) sp. 5, collected from Cooke Point on the northern coastline of Western Australia. Sodium channel and saxiphilin based radio-receptor assays detected saxitoxin-like binding in octopi extracts.
Robertson, Alison   +4 more
openaire   +3 more sources

Differentiation of the actions of tetrodotoxin and saxitoxin

Toxicon, 1967
Abstract While tetrodotoxin and saxitoxin are very similar in their actions, they can be differentiated biologically by the observation that newts of the genus Taricha are resistant to tetrodotoxin but not to saxitoxin. The resistance of these newts is due to a remarkable insensitivity of the somatic motor nerves to tetrodotoxin.
C Y, Kao, F A, Fuhrman
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Occurrence of saxitoxin in puffer fish

Toxicon, 1984
Three species of puffer fish, Takifugu poecilonotus, T. vermicularis and T. radiatus, were examined for the presence of toxic components other than tetrodotoxin. Saxitoxin, a paralytic shellfish toxin, was found in the livers, ovaries and digestive tracts of the first two species but not in the last species.
M, Nakamura, Y, Oshima, T, Yasumoto
openaire   +2 more sources

Chemosensors for the Marine Toxin Saxitoxin

Journal of the American Chemical Society, 2002
Eleven anthracylmethyl crown ethers have been synthesized and evaluated as fluorescence sensors for the marine toxin saxitoxin. Fluorescence enhancement data are consistent with a 1:1 binding complex for all crowns. The binding constants are in the range of 10(4) M(-)(1) in ammonium phosphate buffer (pH 7.1) in 80% ethanol solvent.
Robert E, Gawley   +7 more
openaire   +2 more sources

ChemInform Abstract: STRUCTURE OF A CRYSTALLINE DERIVATIVE OF SAXITOXIN. STRUCTURE OF SAXITOXIN

Chemischer Informationsdienst, 1976
AbstractAufgrund der 13C‐NMR‐Spektroskopie liegt Saxitoxin, das Gift von Schalentieren, in wäß‐ rigen Lösungen als Hydrat vor.
JON BORDNER   +3 more
openaire   +1 more source

Total Synthesis of (−)‐ and (+)‐Decarbamoyloxysaxitoxin and (+)‐Saxitoxin

Chemistry – An Asian Journal, 2009
AbstractPlaying the sax: The enantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) are reported. A new methodology was developed for the synthesis of STXs, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine.magnified imageEnantioselective total syntheses of ...
Osamu, Iwamoto   +2 more
openaire   +2 more sources

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