Prymnesin-B1 is a chemical with the molecular formula C
91H
132ClNO
34. It is a member of the prymnesins, a class of ladder-frame polyether phycotoxins made by the alga Prymnesium parvum. It is known to be toxic to fish. It is a so called "B-type" prymnesin, which differ in the number of backbone cycles when compared to A-type prymnesins like prymnesin-2.[1]
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Names | |
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IUPAC name
1-((2R,3S,4R,5S,6R)-6-((2R,2'S,3'R,4aS,4'aR,6S,6'S,7R,8S,8aR,8'S,8'aS)-6'-(2-((2R,4aS,6S,7R,8aR)-6-((2S,4aR,5aS,6aR,7aS,10R,11aR,12aS,13aR,15S,15aS)-10-((1E,3E,8E,10E,18E)-6-amino-19-chlorononadeca-1,3,8,10,18-pentaen-12,16-diyn-1-yl)-15-hydroxyoctadecahydropyrano[3,2-b]pyrano[2,3:5',6']pyrano[2',3':5,6]pyrano[2,3-f]oxepin-2-yl)-7-methyloctahydropyrano[3,2-b]pyran-2-yl)-2-hydroxyethyl)-3',7,8,8'-tetrahydroxyhexadecahydro-[2,2'-bipyrano[3,2-b]pyran]-6-yl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexadeca-13,15-diyne-2,4,6,7,8,9,10-heptaol
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Identifiers | |
3D model (JSmol)
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PubChem CID
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Properties | |
C91H132ClNO34 | |
Molar mass | 1819.48 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structures
editPrymnesins-B1 is formed of a large polyether polycyclic core with several conjugate double and triple bonds, chlorine and nitrogen heteroatoms and a single sugar moiety consisting of α-D-galactopyranose.
Biosynthesis
editThe backbone of B-type prymnesins like prymnesin-B1 is reportedly made by giant polyketide synthase enzymes dubbed the "PKZILLAs"[2][3].
See also
editReferences
edit- ^ Rasmussen, Silas Anselm; Meier, Sebastian; Andersen, Nikolaj Gedsted; Blossom, Hannah Eva; Duus, Jens Øllgaard; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld (2016-08-23). "Chemodiversity of Ladder-Frame Prymnesin Polyethers in Prymnesium parvum". Journal of Natural Products. 79 (9). American Chemical Society (ACS): 2250–2256. doi:10.1021/acs.jnatprod.6b00345. ISSN 0163-3864. PMID 27550620.
- ^ Kuhl, Heiner; Strassert, Jürgen F.H.; Čertnerová, Dora; Varga, Elisabeth; Kreuz, Eva; Lamatsch, Dunja K.; Wuertz, Sven; Köhler, Jan; Monaghan, Michael T.; Stöck, Matthias (2024). "The haplotype-resolved Prymnesium parvum (type B) microalga genome reveals the genetic basis of its fish-killing toxins". Current Biology. Elsevier BV. doi:10.1016/j.cub.2024.06.033. ISSN 0960-9822.
- ^ Fallon, Timothy R.; Shende, Vikram V.; Wierzbicki, Igor H.; Pendleton, Amanda L.; Watervoort, Nathan F.; Auber, Robert P.; Gonzalez, David J.; Wisecaver, Jennifer H.; Moore, Bradley S. (2024-08-09). "Giant polyketide synthase enzymes in the biosynthesis of giant marine polyether toxins". Science. 385 (6709): 671–678. doi:10.1126/science.ado3290. ISSN 0036-8075.