Prymnesin-1

Prymnesin-1
Names
IUPAC name
77‐Amino‐6,35,90‐trichloro‐17,21:22,26:25,29:30,34:33,37:38,42:41,45:46,50:49,53:54,58:57,62:61,65:64,68:67,71‐tetradecaepoxy‐52‐methyl 14‐(5‐hydroxymethyl‐3,4‐dihydroxy‐2‐oxolanyloxy)‐9‐[5‐(1,2‐dihydroxyethyl)‐3,4‐dihydroxy‐2‐oxolanyloxy]‐13‐(3,4,5‐trihydroxytetrahydro‐2H‐pyran‐2‐yloxy)‐72,74,79,81,89‐nonacontapentene‐1,3,83,87‐tetryne‐7,8,10,11,15,18,19,20,23,24,31,39,43,59‐tetradecol
Other names
PRM1[1]
Identifiers
3D model (JSmol)
  • InChI=1S/C107H154Cl3NO44/c1-3-4-15-23-49(109)79(122)85(128)102(155-107-92(135)89(132)100(154–107)57(120)43-112)81(124)51(114)35-77(149-105-90(133)80(123)58(121)45-136-105)99(153-106-91(134)83(126)78(44-113)150-106)54(117)38-73-82(125)84(127)86(129)103(148-73)104-88(131)87(130)101-65(147–104)31-30-64(146–101)96-55(118)39-75-94(151-96)50(110)34-74(143-75)97-56(119)40-76-98(152-97)53(116)36-67(142-76)60-26-27-61-66(138-60)33-46(2)93(144-61)62-28-29-63-95(145-62)52(115)37-68-70(140-63)42-71-72(141-68)41-69-59(139-71)25-24-48(137-69)22-18-14-17-21-47(111)20-16-12-10-8-6-5-7-9-11-13-19-32-108/h1,8,10,12,14,16-19,22,32,46-107,112-135H,7,9,20-21,23-31,33-45,111H2,2H3/b10-8?,16-12?,17-14?,22-18?,32-19-
    Key: JWYXXCZNFFQYGQ-UOMKELITSA-N
  • C#CC#CC[C@H](Cl)C(O)C(O)C(O[C@@H]1O[C@]([C@@H](CO)O)([H])[C@H](O)[C@H]1O)C(O)C(O)CC(O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)CO2)C(O[C@@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C(O)C[C@@]([C@@H](O)[C@@H](O)[C@@H]4O)([H])O[C@@]4([H])[C@@]5([H])O[C@]6([H])[C@@](O[C@]([C@]7([H])[C@H](O)C[C@](O[C@]([C@@]8([H])O[C@]([C@@H](O)C[C@@]([C@]9([H])O[C@@](C[C@@H](C)[C@]([C@@]%10([H])O[C@@]%11([H])[C@@H](O)C[C@@]%12([H])O[C@@]%13([H])C[C@@]%14([H])O[C@@]([H])(/C=C/C=C/C[C@@H](N)C/C=C/C=C/C#CCCC#C/C=C/Cl)CC[C@]%14([H])O[C@]%13([H])C[C@]%12([H])O[C@]%11([H])CC%10)([H])O%15)([H])[C@]%15([H])CC9)([H])O%16)([H])[C@@]%16([H])C[C@@H]8O)([H])C[C@@H]%17Cl)([H])[C@@]%17([H])O7)([H])CC6)([H])[C@@H](O)[C@H]5O
Properties
C107H154Cl3NO44
Molar mass 2264.72 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prymnesin-1 is a chemical with the molecular formula C
107H
154Cl
3NO
44. 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 C208516H334220N60758O63313S1733,[7] making it the largest known protein.[8][9] It has a molar mass of 4760921.41 g·mol−1.

See also

References

  1. ^ a b c 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. Bibcode:1999JAChS.121.8499I. doi:10.1021/ja991740e.
  2. ^ 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.
  3. ^ Walter, Julia (8 February 2024). "Oder River disaster: What is known about the alga Prymnesium parvum? | IGB". www.igb-berlin.de. Retrieved 8 March 2026.
  4. ^ Manning SR, La Claire JW (2010). "Prymnesins: toxic metabolites of the golden alga, Prymnesium parvum carter (Haptophyta)". Marine Drugs. 8 (3): 678–704. doi:10.3390/md8030678. PMC 2857367. PMID 20411121.
  5. ^ 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. Bibcode:2016JNAtP..79.2250R. doi:10.1021/acs.jnatprod.6b00345. PMID 27550620.
  6. ^ 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. Bibcode:2024Sci...385..671F. doi:10.1126/science.ado3290. ISSN 0036-8075. PMC 11416037. PMID 39116217.
  7. ^ "Expasy - ProtParam". web.expasy.org. Retrieved 2025-06-24.
  8. ^ Nield, David (2024-08-09). "Fish-Killing Toxin Sets New Record in Just How Big a Protein Can Get". ScienceAlert. Retrieved 2024-08-11.
  9. ^ ScienceAdviser: Largest protein described to date helps algae craft deadly toxins (Report). 2024-08-09. doi:10.1126/science.ads3671.
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