Maitotoxin
Names | |
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Preferred IUPAC name
Disodium (12S,14aR,15aS,16aR,17aS,18Z,110aR,111aS,112aR,113aS,114aR,116R,117R,118aS,119aR,121aS,122aR,123aS,124aR,125aS,126aR,127aS,22S,24aR,25aS,26aR,27aS,28aR,29aS,211R,212R,213aR,214S,214aS,215aR,217aS,218aR,219aS,32R,33R,34aS,36S,37R,38R,38aS,5R,7R,82S,83R,84aS,86R,87R,88R,88aS,92R,93R,94R,94aS,95aS,96aR,97aS,98R,99R,910S,911aR,912aS,913aR,914R,914aR,11S,12R,132S,133R,134S,134aS,135aR,136aS,137aR,138S,138aS,1310S,1311R,1312aR,1313aS,1314aR,1315aS,1317R,1317aR)-12-[(1S,2R,4R,5S)-1,2-dihydroxy-4,5-dimethyloct-7-en-1-yl]-117,211,214,33,37,38,5,7,83,87,88,93,94,98,914,11,12,133,134,138,1311,1317-docosahydroxy-14a,15a,16a,114a,116,119a,121a,122a,25a,27a,29a,214a,217a,1313a,1315a-pentadecamethyl-132-[(2R,3R,4R,7S,8R,9R,11R,13E)-3,8,11,15-tetrahydroxy-4,9,13-trimethyl-12-methylidene-7-(sulfonatooxy)pentadec-13-en-2-yl]-13,14,14a,15a,16,16a,17a,110,110a,111a,112,112a,113a,114,114a,116,117,118,118a,119a,120,121,121a,122a,123,123a,124a,125,125a,126a,127,127a,22,23,24,24a,25a,26,26a,27a,28,28a,29a,210,211,212,213a,214,214a,215a,216,217,217a,218a,219,219a,32,33,34,34a,36,37,38,38a,82,83,84,84a,86,87,88,88a,93,94,94a,95a,96,96a,97a,98,99,910,911a,912,912a,913a,914,914a,133,134,134a,135a,136,136a,137a,138,138a,1310,1311,1312,1312a,1313a,1314,1314a,1315a,1316,1317,1317a-octahectahydro-12H,92H,132H-1(16)-pyrano[2′′′ ′,3′′′ ′:5′′′,6′′′]pyrano[2′′′,3′′′:6′′,7′′]oxepino[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[3,2-b]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[2,3-g]oxocina-2(2,12)-bis(pyrano[2′′,3′′:5,6]pyrano[2′,3′:5,6]pyrano)[3,2-b:2′,3′-f]oxepina-13(10)-pyrano[3,2-b]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[2,3-f]oxepina-9(2,10)-dipyrano[2,3-e:2′,3′-e′]pyrano[3,2-b:5,6-b′]dipyrana-3,8(2,6)-bis(pyrano[3,2-b]pyrana)tridecaphan-99-yl sulfate | |
Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.227.039 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C164H256O68S2Na2 | |
Molar mass | 3422 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Maitotoxin (MTX) is an extremely potent
ciguateric fish Ctenochaetus striatus—called "maito" in Tahiti
—from which maitotoxin was isolated for the first time. It was later shown that maitotoxin is actually produced by the dinoflagellate Gambierdiscus toxicus.
Mechanism of toxicity
Maitotoxin activates extracellular
cell lysis.[5] Maitotoxin can indirectly activate calcium-binding proteases calpain-1 and calpain-2, contributing to necrosis.[6] The toxicity of maitotoxin in mice is the highest for nonprotein toxins: the LD50 is 50 ng/kg.[7]
Molecular structure
The
amphipathic structure.[8][9][10] Its structure was established through analysis using nuclear magnetic resonance at Tohoku University, Harvard University and the University of Tokyo in combination with mass spectrometry, and synthetic chemical methods. However, Andrew Gallimore and Jonathan Spencer have questioned the structure of maitotoxin at a single ring-junction (the J–K junction), based purely on biosynthetic considerations and their general model for marine polyether biogenesis.[11] K. C. Nicolaou
and Michael Frederick argue that despite this biosynthetic argument, the originally proposed structure could still be correct.
[12] The controversy has yet[needs update] to be resolved.
Biosynthesis
The molecule is produced in nature via a polyketide synthase pathway.[11]
Total synthesis
Since 1996 the Nicolaou research group is involved in an effort to synthesise the molecule via total synthesis[13][14][15][16] although as of 2015 the project is on hold due to lack of funding.[17]
See also
References
- ^ "MSDS: VX". www.ilpi.com. Retrieved 2022-09-29.
- PMID 3182760.
- PMID 6871549.
- PMID 19794142.
- PMID 11231888.
- PMID 8660700.
- PMID 10495469.
- .
- .
- .
- ^ PMID 16767782.
- PMID 17469088.
- PMID 17943950.)
{{cite journal}}
: CS1 maint: multiple names: authors list (link - PMID 18481856.
- PMID 20415445.
- PMID 25374117.
- ^ Chemistry's toughest total synthesis challenge put on hold by lack of funds Katrina Kramer 15 January 2015 Chemistry World http://www.rsc.org/chemistryworld/2015/01/chemistry-grandest-total-synthesis-challenge-maitotoxin-put-hold-lack-funds
Further reading
- JP JOSHI, Maitland (2004). Organic Chemistry, Third Edition. W. W. Norton & Company. ISBN 978-0-393-92408-4.