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)
  • 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).

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).

  1. ^ a b 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.
  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.