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
Identifiers
CAS Number	168180-17-4;
3D model (JSmol)	Interactive image;
PubChem CID	102510994;
CompTox Dashboard (EPA)	DTXSID201044366 ;
	SMILES 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
Chemical formula	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).

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]^[3] There are three forms of prymnesin known, prymnesin 1 and 2, differing in their glycosylation, and prymnesin B1^[4] differing in backbone.

Biosynthesis

The backbone of A-type prymnesins like prymnesin-1 is reportedly made by giant polyketide synthase enzymes dubbed the "PKZILLAs"^[5].PKZILLA-1 and PKZILLA-2 have been identified with the first consisting of 45,212 amino acids making it the largest known protein.^[6]^[7]

References

^ ^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. doi:10.1021/ja991740e.
^ 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.
^ 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.
^ 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.
^ 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.
^ Nield, David (2024-08-09). "Fish-Killing Toxin Sets New Record in Just How Big a Protein Can Get". ScienceAlert. Retrieved 2024-08-11.
^ ScienceAdviser: Largest protein described to date helps algae craft deadly toxins (Report). 2024-08-09. doi:10.1126/science.ads3671.

[IgarashiSatake1999-1] 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.

[MorohashiSatake2001-2] 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] 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.

[RasmussenMeier2016-4] 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.

[k506-5] 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.

[6] Nield, David (2024-08-09). "Fish-Killing Toxin Sets New Record in Just How Big a Protein Can Get". ScienceAlert. Retrieved 2024-08-11.

[7] ScienceAdviser: Largest protein described to date helps algae craft deadly toxins (Report). 2024-08-09. doi:10.1126/science.ads3671.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Prymnesin-1

Contents

Structures

Biosynthesis

See also

References

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
CAS Number	168180-17-4
3D model (JSmol)	Interactive image
PubChem CID	102510994
CompTox Dashboard (EPA)	DTXSID201044366
SMILES 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
Chemical formula	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