Chemistry:Prymnesin-1
Prymnesin-1 is a chemical with the molecular formula C107H154Cl3NO44. It is a member of the prymnesins, a class of hemolytic phycotoxins made by the alga Prymnesium parvum.[1][2] It is known to be toxic to fish, causing mass fish deaths around the world, including in Texas and England, or in 2022 in the border region of Germany and Poland (Oder).[3]
Structures
Prymnesin-1 is formed of a large polyether polycyclic core with several conjugate double and triple bonds, chlorine and nitrogen heteroatoms and O-linked sugar moieties including α-D-ribofuranose, α-L-arabinopyranose, and β-D-galactofuranose, unlike the single linked α-L-xylofuranose of prymnesin-2.[1][4] There are three forms of prymnesin known, prymnesin 1 and 2, differing in their glycosylation, and prymnesin B1[5] differing in backbone.
Biosynthesis
The backbone of A-type prymnesins like prymnesin-1 is reportedly made by giant polyketide synthase enzymes dubbed the "PKZILLAs" of which PKZILLA-1 and PKZILLA-2 are known.[6] PKZILLA-1 is composed of 45,212 amino acids with a chemical formula of C
208516H
334220N
60758O
63313S
1733,[7] making it the largest known protein.[8][9] It has a molar mass of 4760921.41 g·mol−1.
See also
- Prymnesin-2
- Prymnesin-B1
- Titin, largest protein in human muscles and the previous largest known protein with 34,350 amino acids.
References
- ↑ 1.0 1.1 Igarashi, Tomoji; Satake, Masayuki; Yasumoto, Takeshi (1999). "Structures and Partial Stereochemical Assignments for Prymnesin-1 and Prymnesin-2: Potent Hemolytic and Ichthyotoxic Glycosides Isolated from the Red Tide Alga Prymnesium parvum". J. Am. Chem. Soc. 121 (37): 8499–8511. doi:10.1021/ja991740e. Bibcode: 1999JAChS.121.8499I.
- ↑ Morohashi, Akio; Satake, Masayuki; Oshima, Yasukatsu; Igarashi, Tomoji; Yasumoto, Takeshi (2001). "Absolute configuration at C14 and C85 in prymnesin-2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga Prymnesium parvum". Chirality 13 (9): 601–605. doi:10.1002/chir.1184. PMID 11579456.
- ↑ Walter, Julia (8 February 2024). "Oder River disaster: What is known about the alga Prymnesium parvum? | IGB" (in en). www.igb-berlin.de. https://www.igb-berlin.de/en/news/oder-river-disaster-what-known-about-alga-prymnesium-parvum.
- ↑ "Prymnesins: toxic metabolites of the golden alga, Prymnesium parvum carter (Haptophyta)". Marine Drugs 8 (3): 678–704. 2010. doi:10.3390/md8030678. PMID 20411121.
- ↑ Rasmussen, Silas Anselm; Meier, Sebastian; Andersen, Nikolaj Gedsted; Blossom, Hannah Eva; Duus, Jens Øllgaard; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld (2016). "Chemodiversity of Ladder-Frame Prymnesin Polyethers in Prymnesium parvum". J. Nat. Prod. 79 (9): 2250–2256. doi:10.1021/acs.jnatprod.6b00345. PMID 27550620. Bibcode: 2016JNAtP..79.2250R.
- ↑ Fallon, Timothy R.; Shende, Vikram V.; Wierzbicki, Igor H.; Pendleton, Amanda L.; Watervoort, Nathan F.; Auber, Robert P.; Gonzalez, David J.; Wisecaver, Jennifer H. et al. (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. PMID 39116217. Bibcode: 2024Sci...385..671F.
- ↑ "Expasy - ProtParam". https://web.expasy.org/cgi-bin/protparam/protparam_bis.cgi?A0AB34IYJ6@noft@.
- ↑ Nield, David (2024-08-09). "Fish-Killing Toxin Sets New Record in Just How Big a Protein Can Get" (in en-US). https://www.sciencealert.com/fish-killing-toxin-sets-new-record-in-just-how-big-a-protein-can-get.
- ↑ (in en) ScienceAdviser: Largest protein described to date helps algae craft deadly toxins (Report). 2024-08-09. doi:10.1126/science.ads3671. https://www.science.org/content/article/scienceadviser-largest-protein-described-date-helps-algae-craft-deadly-toxins.
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