98:
157:
24:
179:
C#CC#CC(Cl)C(O)C(O)C(O1O((CO)O)()(O)1O)C(O)C(O)CC(O2(O)(O)(O)CO2)C(O3(O)(O)(CO)O3)C(O)C((O)(O)4O)()O4()5()O6()(O(7()(O)C(O(8()O((O)C(9()O(C(C)(%10()O%11()(O)C%12()O%13()C%14()O()(/C=C/C=C/C(N)C/C=C/C=C/C#CCCC#C/C=C/Cl)CC%14()O%13()C%12()O%11()CC%10)()O%15)()%15()CC9)()O%16)()%16()C8O)()C%17Cl)()%17()O7)()CC6)()(O)5O
590:
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".
454:
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
421:
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
40:
77âAminoâ6,35,90âtrichloroâ17,21:22,26:25,29:30,34:33,37:38,42:41,45:46,50:49,53:54,58:57,62:61,65:64,68:67,71âtetradecaepoxyâ52âmethyl 14â(5âhydroxymethylâ3,4âdihydroxyâ2âoxolanyloxy)â9ââ13â(3,4,5âtrihydroxytetrahydroâ2
367:
The backbone of A-type prymnesins like prymnesin-1 is reportedly made by giant polyketide synthase enzymes dubbed the "PKZILLAs".PKZILLA-1 and PKZILLA-2 have been identified with the first consisting of 45,212
545:
Rasmussen, Silas Anselm; Meier, Sebastian; Andersen, Nikolaj
Gedsted; Blossom, Hannah Eva; Duus, Jens Ăllgaard; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld (2016).
335:
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
327:. 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).
714:
171:
651:
359:. There are three forms of prymnesin known, prymnesin 1 and 2, differing in their glycosylation, and prymnesin B1 differing in backbone.
627:
256:
694:
135:
44:âpyranâ2âyloxy)â72,74,79,81,89ânonacontapenteneâ1,3,83,87âtetryneâ7,8,10,11,15,18,19,20,23,24,31,39,43,59âtetradecol
724:
699:
689:
684:
704:
36:
709:
679:
152:
729:
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398:, largest protein in human muscles and the previous largest known protein with 34,350 amino acids.
608:
572:
527:
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428:
323:
655:
600:
562:
517:
507:
468:
436:
194:
74:
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496:"Prymnesins: toxic metabolites of the golden alga, Prymnesium parvum carter (Haptophyta)"
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522:
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123:
673:
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652:
ScienceAdviser: Largest protein described to date helps algae craft deadly toxins
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628:"Fish-Killing Toxin Sets New Record in Just How Big a Protein Can Get"
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Except where otherwise noted, data are given for materials in their
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547:"Chemodiversity of Ladder-Frame Prymnesin Polyethers in
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271:is a chemical with the molecular formula
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7:
715:Halogen-containing natural products
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14:
494:Manning SR, La Claire JW (2010).
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253:(at 25 °C , 100 kPa).
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200:
1:
568:10.1021/acs.jnatprod.6b00345
372:making it the largest known
626:Nield, David (2024-08-09).
347:, unlike the single linked
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35:
30:
21:
310:. It is a member of the
660:10.1126/science.ads3671
605:10.1126/science.ado3290
654:(Report). 2024-08-09.
345:ÎČ-D-galactofuranose
341:α-L-arabinopyranose
243: g·mol
18:
695:Secondary alcohols
257:Infobox references
16:
725:Conjugated diynes
700:Conjugated enynes
599:(6709): 671â678.
549:Prymnesium parvum
513:10.3390/md8030678
473:10.1002/chir.1184
457:Prymnesium parvum
441:10.1021/ja991740e
435:(37): 8499â8511.
429:J. Am. Chem. Soc.
424:Prymnesium parvum
352:
324:Prymnesium parvum
321:made by the alga
265:Chemical compound
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136:CompTox Dashboard
99:Interactive image
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690:Primary alcohols
685:Polyether toxins
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337:α-D-ribofuranose
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506:(3): 678â704.
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467:(9): 601â605.
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353:-xylofuranose
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314:, a class of
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635:. Retrieved
632:ScienceAlert
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555:J. Nat. Prod
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500:Marine Drugs
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391:Prymnesin-B1
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363:Biosynthesis
334:
322:
268:
267:
58:Identifiers
50:Other names
41:
17:Prymnesin-1
710:Halohydrins
680:Phycotoxins
386:Prymnesin-2
370:amino acids
357:prymnesin-2
319:phycotoxins
269:Prymnesin-1
188:Properties
75:168180-17-4
730:Glycosides
674:Categories
637:2024-08-11
403:References
331:Structures
312:prymnesins
232:Molar mass
86:3D model (
65:CAS Number
37:IUPAC name
613:0036-8075
461:Chirality
316:hemolytic
124:102510994
577:27550620
532:20411121
481:11579456
380:See also
593:Science
523:2857367
374:protein
111:PubChem
720:Amines
611:
575:
530:
520:
479:
343:, and
172:SMILES
31:Names
396:Titin
88:JSmol
609:ISSN
573:PMID
528:PMID
477:PMID
52:PRM1
656:doi
601:doi
597:385
563:doi
518:PMC
508:doi
469:doi
459:".
437:doi
433:121
426:".
355:of
287:154
278:107
241:.72
239:264
210:154
204:107
141:EPA
114:CID
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559:79
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411:^
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349:α-
339:,
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300:NO
291:Cl
225:44
213:Cl
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439::
351:L
296:3
282:H
273:C
237:2
222:O
219:N
216:3
207:H
201:C
143:)
139:(
90:)
42:H
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